Towards the end of the 1990s, the term "startup" became more of a philosophy than a descriptor. That's when the implications, both good and bad, manifested.
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I asked a bunch of venture capital and angel investors what works, what hurts, and what they look for from the very first contact with an entrepreneur.
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In any crowded field of consumer-facing transactional apps, an app's UX must be focused on these rules of engagement - and awareness and conversion and retention.
I used to think salary didn't matter, because I love what I do. But I've learned that it's critical to get employee pay right, both what you're taking home and what you're handing out.
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The most heartbreaking stories from early entrepreneurs is when they have this great startup idea and they're already paying a software developer to build it out.
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Entrepreneurs sometimes don't realize they can learn just as much from their successes as from their failures, provided they take the time to extract the lessons.
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Startup growth isn't leapfrogging from big win to big win. It's chaining together all the wins, small to medium to large. Here's how to do that.
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One of the most difficult skills for any leader, innovator, or entrepreneur to master is solid decision making. Here are three things to consider when making a big decision.
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I strongly believe raising startup funding through customer sales is the best option, and in a lot of cases, it should be the only option.
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In 2021, there were over 60 startup unicorns minted in each of several months that year. That's hundreds of companies valued over $1 billion each. Where are those unicorns now?
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When I get called in to fix a struggling startup, here are the top things I have to undo, the statuses I have to un-quo, the corporate traps that startups keep falling into.
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If you're not losing customers, you're not growing. You may on that slow train to nowhere, but you're not building a business that's increasing in value.
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Expensive software development without customer demand often leads to expensive failures. So how do you decide what to automate and when?
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Starting companies would be the most fun and satisfying career ever - if I didn't have to figure out how to fund them.
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In my line of work, I come into contact with a lot of rich and successful people. And they tend to tell me things they shouldn't.
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One interpretation of failure is about building on progress, the other more traditional interpretation is the definition of insanity. What's the difference?
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Just like always, future entrepreneurs are going to exploit recent technology advancements, this time in a singular quest to entertain us.
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I’ve got way too much respect for your intelligence to just barf out a list of predictions that no one will fact check me on in December.
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If you want to be a successful entrepreneur, you need to stop listening to what everyone says you should do.
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If you want your business to be in the right place at the right time, you've got to get your business to the right place for when the right time happens.
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Product market fit is not a science to be decoded. It's just a term and a target. But aiming at that target should never be guesswork.
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An iconic media brand published AI content from fake writers, but the more troubling issue is why they did it
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Poor leadership hits toxic levels of incompetence when the actions of the leader start to consistently work against the progress of the company.
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Omegle's rise and demise probably signals that the internet will never be anything better than what it has become.
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What WeWork's bankruptcy means for the rest of us entrepreneurs who don't have Adam Neumann's amazing hair or look great in a black turtleneck.
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Instead of figuring out ways to add value, a lot of marketplaces just started selling ads. Here's why that model isn't sustainable.
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Every startup's product has its genesis in the company's vision, mission and product position. With that in mind, let's start rethinking our product from the top.
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It's time for VC investors and the press to stop propping up reheated business models based on chasing trends and in-the-moment customer feedback.
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A startup idea isn't worth anything. It's the execution that matters. But sometimes, the execution isn't worth anything either. And that needs to be fixed.
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I've been skeptical of Generative AI because I already know where this is headed. I know the right way to use the tech. And it has to do with the end of SaaS.
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Does AI really deserve the fervor, and more importantly, the investment capital being poured into this somewhat new and novel technology? And why now?
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When startup founders and entrepreneurs take big swings, some people are going to push back. That's what haters do. Here's how you spot them in the wild.
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Venture capital investment into the creator economy hints at a lot of what's wrong with the VC model right now, especially at the highest levels.
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If you really want to solve the problem of trolls, cyber-bullying, and misinformation on the web, you have to ask: Why do those things exist in the first place?
Here are the top four ways that I've seen a change in a startup's priorities to accommodate a bandwagon trend like AI can destroy that company from the inside.
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Failure is not a badge of courage. Failure is like death, but in a video game. You can get a do over, so the value of failure comes from the lessons you learn.
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Getting permission to use customer company badges and testimonials follows a Catch-22 rule stating "The more important a thing is to have, the harder it is to get."
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Project management disguised as product management won't FIX a broken growth cycle. What it actually does is codify the FLAWS in the company's processes.
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No user likes to do input. This is why something as relatively simple as Generative A.I. can make a huge difference as users start to reject all those SaaS screens.
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If you're building the common startup, the ecosystem is set up to work against you. If you want to succeed, you have to build the uncommon startup instead.
When you're writing and your mission is to make the words mean something, you need to constantly refresh and reinvent.
If I were to choose one nugget of advice that I would give to every startup founder, it would be this. "Do not fail. Until you absolutely have to."
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I got an email last week from an investor that was basically a pitch to sell me services with a carrot of potential investment dangled to help sweeten the deal.
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Let's talk about where plugging A.I. into your own business framework makes sense, using the most recent A.I. variant: GPTs.
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It's becoming increasingly obvious that the A.I. business and startup bandwagon is running out of room. It's time to hop on that money train. Right?
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I'm a huge fan of the democratization of technology that allows a non-technical founder to get their ideas into the arena of high-tech entrepreneurship.
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The next wave of Generative A.I. will surely be providing answers to more complex questions. The money will be in automating the creation of those questions.
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When you're a startup leader, you're not trying to become the best at what you do, but rather the best at building the business that does what you do.
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I'm not going to tell you whether or not to shut down your startup. But I will tell you what I've done, because I've been there at least a dozen times.
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Conventional wisdom has always taught the innovator to focus on being great at one thing, then build on that greatness. That's no longer true.
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Bootstrapping a startup with $10,000 may seem like a lot of money or nowhere near enough. Regardless, the trick isn't how much you spend, it's how you spend it.
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Hiring a team to help build one of the first ever Generative A.I. platforms, I discovered the skills you need to be successful with A.I., they're not about writing code.
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The key to avoid being replaced by A.I. isn't to get good at what A.I. does. Far from it. The key is to get great at the things A.I. sucks at.
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Bravado fuels startups to take enough risks to start growing. But as soon as things become real, they realize that their bravado is just that, and they panic.
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Mistral AI just raised $113 million exactly one month after formation. How long does it really take for a startup to achieve "overnight success"?
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If I come up with what I believe to be a great startup idea, and if I can't put it into one of these 4 categories, I've learned to bury the idea before it buries me.
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The truth is that most startups do pricing wrong, and they almost always err on the side of underpricing. It's a common mistake made in the name of customer acquisition.
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I'll use Amazon as the late-stage example and I'll use two of my own startup experiences to show you how to dominate by thinking big and acting small right now.
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An overview of which parts of your startup's operations should be automated quickly and inexpensively by third-party platforms.
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It's never been easier to rely on no-code and low-code tech to build a product and start generating revenue. You can get started for under $100.
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The only person who can tell you what your startup is actually worth is the person writing the check to buy it. But let's figure out a better answer.
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Micromanagement is a dirty word. So why do most startup leaders micromanage their teams? Here are the reasons why and how to avoid it happening to you.
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Promising the impossible is a surefire way for a startup to succeed, provided it delivers. If not, then it's a one-way ticket to lawyers, judges, and charges.
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The job that Generative A.I. is going to take is probably not yours. And you might get a laugh when I tell you which jobs are immediately in danger of being erased.
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If you want real, valuable, revenue-generating customers, your app has to walk a perfectly balanced line between customer friction and data collection.
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Sometimes a startup side hustle is not a bold-face scam, but a scheme to take your money by selling you on an idea to game a system for pure profit.
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The immediate problem with ChatGPT and Generative A.I. is that words mean things. Unless you're using ChatGPT. Then words become useless. Even dangerous.
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Here's a hard truth. No legitimate startup ever goes from a handful of sales to $1,000,000 in revenue overnight. Here are all the reasons I've seen sales slow.
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If Generative AI has suddenly become so pervasive, there will be a secondary effect that increases the scarcity and the value of uniquely human knowledge.
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There's one critical area where low-tech can destroy your business if you don't do it right or you wait too long to come back and fix it.
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You can still make a lot of money with A.I., but it's not snap-your-fingers money, it's more like try-and-fail-a-dozen-times money.
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Hiring talent that doesn't live up to the claims made on a resume and in an interview can be a company killer. Here's how to spot the warning signs.
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The less time you spend conforming to a someone else's definition of a startup is more time spent finding customers and generating value and revenue.
When investors consider investing in a startup, they don't want to be writing checks to support the antics of a rock star.
What's the opposite of fit? Tell me it's not, "A person that no one would ever want to work with." Then let's talk about better ways to build a team.
It's easy for startup founders to figure out we were lazy or made the wrong decision. We rarely check whether our lack of belief was the root cause of failure.
Desperation is a quirky and nagging little fault because you can't see it unless you're looking for it. But once you start looking for it, you'll see it everywhere.
The startup gold rush is on with Natural Language Generation and the recent commercialization breakthrough heralded with ChatGPT.
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In business, there are going to be enough unknowns once you hit the pavement to put both your success or failure in a world of doubt.
The fastest path for a startup to create recurring revenue is by offering a subscription. But you have to devise pricing that keeps your customer base growing.
I see startup founders and other business visionaries with all the talent in the world fail because they can't get out of their own, altruistic way.
In almost every startup's lifecycle, there comes one or more pivot points when much bigger opportunities are possible. But it's going to cost money to get there.
In business, the cost of sticking with a model that isn't returning results is financial, psychological, and impacts many more people than just you.
Just because you can envision selling a customer a product, that doesn't mean they'll buy it.
There's a certain level of business success that I will never achieve, because I won't pull the trigger on being cutthroat in order to get there.
Startup founders tend to build a business in the early stage that works economically at a million customers but is a money pit at a hundred customers.
Like any good thing, "business" can be taken too far. It can be done wrong so many times that the wrong ways become perceived to be the norm.
In all my years of experience running startups, I've never seen a failure go down because one morning everyone woke up and the money was gone.
If you want customers for life, turn your startup's onboarding process into a customer success process with this simple 6-step checklist.
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Hey. Startup founders and innovators. All that "you-don't-work-hard-enough" tough love advice is bullshit. And I'll counterpunch it point by point.
If you don't fire your startup's worst customers, you're probably not innovating, growing, or even running the business you originally started.
Before you succeed at anything, you have to be honest about your motivation. Here's how to prevent it from being defined for you.
Every time I see a blog post that's been written with ChatGPT, I get angry - not because AI might replace writers, but because it was so easy to replace them.
Go-to-market strategy is more than just a landing page and a credit card form. Here's what's usually missing.
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Great content can be rocket fuel for sales. But when that content is delivered into a vacuum, it's a waste of talent, effort and money.
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In almost all the cases where I've seen content marketing fail, the primary reason was the lack of a coherent, dead simple content marketing plan.
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Your company can make huge gains leading your customers down the path toward success, a path that starts with your release management process.
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Proper product release management reduces rework and generally improves the understanding of what your company does and how it hits your customers and prospects.
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Before your startup begins raising venture capital, every penny of that money should be earmarked to an item that will result in a sizable return.
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With all the recent hype about ChatGPT, I thought I'd revisit and update one of my early pandemic posts about startups trying to cash in on trends.
A high Net Prompter Score (NPS) can become a good problem to have. An experienced founder is always skeptical of easy success, so here are the mistakes I might have made.
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The success of a startup is based on the brilliance of the idea and the excellence of the execution, not how much money you can throw at it.
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We all know about CNN+, Google Glass, and Amazon Fire Phone. Were those brands powerful? Absolutely. Were those products marketed poorly? No. Should you emulate them? Most definitely not.
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We've covered theory, first touch, and landing page. Here's what to do with the prospect when they show up at your website and give you their email address.
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When discussing marketing and sales strategy in the digital age, it helps to first ask this question: Why does most startup marketing fail?
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These are the four frustration-borne behaviors I've seen lead to failure most often, why they happen, and what I do to avoid them.
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Great startup ideas are a dime a dozen. Great ideas executed to perfection are diamonds in the rough. The difference is often stated but rarely discussed.
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One of the best ways to kill a startup is to spend time on activities that produce a low return on the time invested. Yet we entrepreneurs do this constantly.
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For entrepreneurs, complexity creep is a natural phenomenon, and it will always happen unless we're proactive about keeping it from happening.
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What goes in a startup's investor pitch deck comes from the investor data room, and the data is produced by making and selling the product.
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Over the years, three massive changes have shaken the startup universe. In 2022, those changes shifted the traditional growth path, possibly permanently.
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The startup malaise phase is enough to make good founders give up. But overnight success requires years of preparation. Don't give up. Do this instead.
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When a startup is trying to break into a market, you need to get ready for "no," because "no" is usually the best possible outcome, and it's where learning starts.
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When building a new product, I'm not interested in what the customer wants. If I figure out what they're doing and why, I can automate it, eliminate it or reinvent it.
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If you're going to have a free tier, you have to make it work like quicksand in the customer funnel. That is, keep customers stuck. In a good way.
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The timing of when a startup founder hands out equity is important. If you get it wrong, you'll wind up with underperforming and over-entitled employees.
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There are a few guidelines every startup founder should follow to increase their chances of landing early investor funding.
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se your product roadmap to break down the path to your ultimate destination into manageable chunks. At each milestone, ask, "Did we do what we said we would do?"
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At startup velocity, a product roadmap has to be flexible, has precious little room for error, and has to be brief and to the point. Here's an example.
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The worst mistake a startup founder can make is to look at any chart that rockets up and to the right and assume that it will stay that way forever.
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Some of the most successful startups began by breaking something and reconfiguring it for another purpose.
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How entrepreneurs can pretty easily get tricked into spending their hard-earned revenue under the guise of a phony investment in their startup.
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When startup growth depends on moving forward all the time, it's difficult to put strategy into action, which must be planned and executed from the goal backwards.
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Entrepreneurs make dumb mistakes mostly because of fear or greed. That makes those mistakes easy to make but hard to learn from. Here's how to get to the lesson.
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The weird thing about this downturn is that it's causing great havoc in some market segments, and it's not even noticeable in others.
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Achieving success with a startup is difficult, but maintaining that success across a wider swath of customers is a different story.
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Too many first time entrepreneurs fall into the trap of trying to launch their business based on what they hear about how startups are supposed to be run.
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When a startup is faced with the threat of a well-funded competitor, there are a few questions that need to be asked, and only a few answers that will work.
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A lot of startups don't think about pricing much before they launch a new product. They do a lot of guessing, and to be fair, a lot of pricing is indeed guesswork.
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After growing several startups from zero to exit, experience has taught me that if you do the same things the same way for too long, the returns will inevitably diminish.
The more professional you try to look in an effort to prove your authenticity bona fides, the more you're going to push customers away.
I've gotten way ahead of myself on the vision, and built this very robust version of my product that's probably six months ahead of its market.
A lot of the hurdles standing between us and what we want to accomplish aren't as big as they seem once you get over them.
The death spiral is a concept I learned from one of my mentors, and it can apply at any time, to any part of a business, or even the business as a whole.
Hiring is hard. When you're a startup with no track record, scant funds, and less than top-of-line resources and benefits, it's usually a nightmare.
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A free-tier strategy can be incredibly effective for bringing in new customers. A poorly executed free-tier strategy can damage your brand forever.
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There’s a lot of misunderstanding around using free trials to find product-market fit. The model can produce tremendous results but also crippling mistakes.
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When your available hours suddenly get reduced to zero, you're faced with hard choices as to what doesn't get done and how much money gets lost.
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No-code is no joke. It may make coding feel like a game, but you can't treat it like one. You need to document everything you do. Here's how.
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A founder should never think of fundraising in terms of the single lump sum of money. You should always think of funding as one raise at a time.
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After every startup success, big or small, there's an immediate period of letdown equal in proportion to the magnitude of the work it took to get there.
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If you don't have a release management process in place, stop everything and create one. Don't wait for that next brilliant idea to die on a vine of apathy.
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One of the most frequent reasons investors reject startup founders is the lack of a coherent plan for the money once it's banked. Let's come up with a plan.
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A startup's greatest limitation is time, and product planning is, at best, a luxury. But without product planning, there is chaos, and mistakes, and rework.
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I got three inbound emails from founders whose initial success turned into a giant problem. Here's how each unraveled and what I would do to avoid it.
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Most entrepreneurs do what they do because they love what they do. And If you truly love what you do, failure isn't failure until you give up.
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The usefulness of your product or service is a metric that's hard to quantify. As a result, a lot of entrepreneurs don't bother trying to measure it at all.
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A case study on how to use a product survey to search for, discover, and enhance where your own product's usefulness can be found.
You can't actually start a company with zero money. I just need to reach the people for whom that seems like that's only path to entrepreneurship.
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Before the startup growth curve can kick in, your focus must come off of the product, because growth is almost always built on a market story.
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Business mistakes always come with lessons, big and small. In the heat of a post-mistake correction, it's tempting to amputate when more surgical solutions will do.
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In almost every case where a startup's requirements process is painful, it's because that process is being done wrong. And it doesn't have to be that way.
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This extremely powerful analog productivity booster was made expendable by the digital revolution, and then made nearly extinct by the shift to remote work.
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Times of economic crisis call for drastic measures. Preemptively right-sizing a workforce and rescinding job offers goes over the limit.
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It's the question I get most often: "How do I get the money I need to fund my startup idea?" And there's a simple answer, once you get past the smokescreens.
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In the digital business era, we rely on a lot of third party tools to help us grow our business. But none of those tools tell me what I need to know.
When imitation crosses the line, the victimless crime actually produces a lot of victims - the people who believe the fake is real. And it never happens by accident.
Customer success can mean different things to different organizations. But it should never mean being everything to everyone to make all customers happy.
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For a young, up-and-coming startup, the sales cycle, for lack of a better word, sucks. It's the single biggest hurdle for any new and unproven company.
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My experience with MVP and no-code has me convinced that raising money for either will eventually become the norm. Here's what you need to establish first.
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These three steps will give you guidelines for creating something tangible to sell, a way to sell it, and a plan for profitability from the start.
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Before you argue with me about the future of crypto, web3, NFTs, and DeFi, let me try to spray a little foam on the (fake money fueled) fire.
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These strategies will help you solidify your own market footing, and make it that much harder for the incumbents to take you out before you take them out.
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I've narrowed down a few proven preventative strategies to proactively protect your startup's ideas and IP, in order from least effective to most.
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The problem with hiring your friends into your startup is that you're assuming that the dynamics from one relationship can translate to the second. This never happens.
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Every entrepreneur has big dreams of massive scale. Most of those big scale dreams are never realized. Here's how to crawl, walk, run your company to scale speed.
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The law of unintended consequences is a nightmare for both startups and mature companies. I believe I know why. And I think I've narrowed down the source of the problem.
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Experienced CEOs do whatever it takes to retain their best people. Because they're the ones who are going to navigate the company through the storm.
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For company goals to actually matter, they must be broken down into actionable steps that everyone understands and whose purpose in furthering the company's mission is clear.
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Asking your startup's customers the right questions, interpreting their feedback, then acting with the proper amount of force - that's a well-tested strategy for market growth.
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Despite how Hollywood portrays the road to startup riches, you'd be surprised how many times a small business quietly evolves into a high-growth venture.
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If your startup's potential is based on a hockey stick head fake or anything that can't be measured in revenue, then yeah, you should probably read those nervous investor memos.
It's easy to think that the big paydays that happen with some startups could happen to any startup. But the truth is that there is no formula for startup success.
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What I've learned over the last two decades about the difference between personal success and business success and why that difference is so important.
When entrepreneurs come up against a skill they don't have experience with, they tend to just not do it. What they should be doing is taking their best hack. Here's why.
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There's one leadership skill that I still suck at - even after 20+ years of founding and leading companies. And I'm not alone. I see this take leaders down repeatedly.
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The transition from startup family to corporate machine creates a culture that relegates the best talent to quiet background cog. They become a silent minority. Then they leave.
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Her startup had raised $3 million, but deadlines weren't being met, runway was burning, investors were frustrated, and customers were angry.
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I've been building and advising no-code startups for years now. And if you want your no-code business to take off, you have to treat no-code as a tool, not a business idea.
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When your startup idea isn't investable, here's what to do, based on my own experience as well as helping dozens of founders, both first-timers and repeat founders.
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I'm not the first to tell you to rest every once in a while. But maybe I'll be the first to give you justification for why it makes great business sense.
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The only way to succeed -- with a startup or any other pursuit -- is to understand what makes you different and be faithful to it. Let's get weird.
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Raising money is a long, difficult process and will take at least six months or more. How do startup CEOs raise money without company growth falling off a cliff?
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What you do or don't do to tap the value of your email list might end up being the difference in eventually finding that elusive product market fit.
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True for any company, team, or project - leadership has three distinct phases. The trick is getting to the right one and staying there as long as you can.
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The barrier to entry for standing up a digital marketplace has fallen. But just because marketplaces startups are easy to start doesn't mean they'll be successful.
People who create reports really like to create reports. People who need to read reports really hate to read reports. This is reaching a tipping point.
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If your startup is truly offering a disruptive product to an exiting customer base, you should be turning a money decision into a time decision.
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Don't fall into the same money trap I see both new and veteran entrepreneurs get caught in over and over again. It all starts with a few bad choices.
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20 years ago, an investor shot down a startup idea of mine because it wasn't "crazy enough." He was right. Here's what happened and what I learned.
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These are the most important learnings I can share after 12 months wrestling a real business into profitable reality without writing any code.
* Featured In Inc. Magazine *
Every startup CEO wants the shiny new relationship to benefit their business, but few want to put in the work necessary to make the relationship valuable.
* Featured In Built In *
An entrepreneur can legitimately start a business, launch a product, and generate revenue or seek investment without risking a ton of upfront capital.
* Featured In Built In *
Innovative startups don't sweat the competition, they change the rules instead. They do this by creating and then dominating a brand new market.
* Featured In Inc. Magazine *
A failed minimum viable product is OK, because you can recover. An impracticable product is the opposite of viable and can be identified by 4 fatal flaws.
* Featured In Inc. Magazine *
A leadership communication strategy shouldn't just keep you out of trouble, it should push you into the kind of trouble that springboards your business to new heights.
* Featured In Built In *
A multi-post guide to help entrepreneurs and innovators start and expand real businesses using no-code tools and platforms. Updated frequently.
The decision to launch a minimum viable product is difficult. These 5 questions address the most critical decision criteria and give your MVP its best chance at success.
* Featured In Inc. Magazine *
Why is most social media marketing awful? Because most people think it's about memes and influencers. Let's build a social media marketing strategy that leads to a purchase.
* Featured In Built In *
The first 30 days of any startup growth plan are a blur, and by the next 30 days, you're off plan. Here's how to get back on track and survive multiple hits.
* Featured In Inc. Magazine *
If the demand for your startup's product is not as rosy as the projections, you might have too much product management and not enough business management.
* Featured In Built In *
A multi-tiered pricing model can help a startup grab quick market share, but that pricing menu can lead to slow sales or no sales at all. Let's identify and fix that.
* Featured In Marker by Medium *
If your startup isn't achieving the kind of sales numbers it should, don't make the mistake of reinventing your product. Take a hard look at your market instead.
* Featured In Inc. Magazine *
When startup founders share their time, resources, and knowledge, the returns can be extraordinary -- if you know how to maximize them properly.
* Featured In Built In *
Every startup employee should take time to help sell and support their own product. It's not for a photo-op, it's actually to help them do their job.
* Featured In Inc. Magazine *
Rapid advancements in no-code and minimum viable product have created opportunity for startups where opportunity didn't previously exist. You need to tap that opportunity.
* Featured In Inc. Magazine *
Outbound email marketing doesn't help a startup target its market. It helps a business accelerate sales within their target market. Here's how.
* Featured In Inc. Magazine *
In a startup, no matter how efficient and motivated you are, the harder you chase the wrong goals, the more time you waste.
* Featured In Built In *
Having built tech for startups for the better part of three decades, I've learned that solving problems with tech almost always creates new problems.
* Featured In Inc. Magazine *
Successful marketing partnerships don't happen like lightning in a bottle. All of the exciting stuff needs to wait until you can show traction.
* Featured In Inc. Magazine *
A strong company culture can promote healthy increases to both the top and bottom line. But all levels of management must be proactively involved in forming it.
* Featured In Inc. Magazine *
Customer success isn't about making your customer happy. It's about making them more successful with your product. It's about change. And change sucks.
* Featured In Built In *
A lot of business owners don't realize that they have almost total control over who their customer is and how much money those customers are willing to spend.
* Featured In Inc. Magazine *
Here are four times a startup tries to raise money too early, and how waiting will increase your odds of getting the funding you actually need.
* Featured In Inc. Magazine *
The dividing line between a successful and unsuccessful startup exit is the value of the equity you're holding onto at the end, not at the beginning.
* Featured In Inc. Magazine *
Every entrepreneur longs for that day when unsolicited investor interest comes knocking and suddenly an idea becomes a funded reality.
I'm going to debunk some conventional wisdom about success and failure in business and entrepreneurship. The truth? Risk tolerance is meaningless.
* Featured In Inc. Magazine *
There's one particular kind of startup shutdown that can be avoided. And it's when the founders let their best intentions get ahead of their best defense.
A superuser is someone from the business side who is intimately familiar with both your customers' problems and how your product solves those problems.
* Featured In Built In *
Investors give a startup a bunch of money to scale, they expect you to hire for critical roles, then they start asking why your burn rate is so high.
* Featured In Inc. Magazine *
I can tell you exactly how to build a better newsletter, as a standalone product startup or as a marketing campaign, by telling you why I set out not to build one.
* Featured In Built In *
In startup, there's a huge difference between creating a culture of hard work and creating a culture of results. One is a path up, the other is a spinning wheel.
* Featured In Inc. Magazine *
Productivity gets sucked out of the company when this kind of meeting culture starts to replace teamwork, communication, and even actual work.
* Featured In Inc. Magazine *
B2X is more than just deciding to offer your product to anyone; it requires a product and sales strategy that can conform to multiple requirements and use cases.
* Featured In Built In *
If you lean into the gig or creator economies too hard, you're going to get burned. It's just a matter of when and how much income is at stake.
* Featured In Built In *
I've started reaching out to bring on more advisors. And I'm running into a problem. A lot of people who claim to be startup experts are condescending as hell.
Should your company pay existing customers to bring in new customers? It depends. Your business might create an army of angry amateur influencers.
* Featured In Inc. Magazine *
It seems obvious, but when your platform is the core of your startup, you're not building software for users, you're creating a product for customers.
* Featured In Inc. Magazine *
This is insight culled from the last 20 years of turning over a lot of stones to find every entrepreneurial edge for my startup.
If you're selling your new product to people you already know, you're setting your business up for death by a million false positives.
* Featured In Inc. Magazine *
There are too many un-taught, would-be successful entrepreneurs going through the startup growth stage walking that fine line of fear and boredom.
* Featured In Inc. Magazine *
All startups say they put the customer first, but their product development process usually undoes that promise. Let's fix that.
* Featured In Built In *
Don't try to build your billion-dollar startup on day one. Instead, work backwards, like television seasons in a series, and write one episode at a time.
* Featured In Inc. Magazine *
No-code tools aren't just for building cute apps. They're becoming essential in scaling companies of all types and sizes, in every industry.
* Featured In Inc. Magazine *
Here's a rough look at how much time it takes to drive a startup to success, based on my experiences with startups that thrived, failed, and stagnated.
* Featured In Inc. Magazine *
I've launched enough Minimum Viable Products to have had my share of bad ones. So here's what I do when I can't figure out what my next step should be.
* Featured In Built In *
This isn't a rant against startup investment. Rather, it's a call to every single founder to keep their focus on maintaining runway. Here's why.
* Featured In Built In *
Here are four ways I've experienced the low-growth to high-growth transformation, either with my own startups, those I've advised, or those I've worked for.
* Featured In Inc. Magazine *
The advice given to entrepreneurs, "Do one thing very well" is dangerously short-sighted. And in some cases, that advice can set up a startup for eventual failure.
A feature is something your product does. A solution is something your customer needs. Startups use cool features to cover up poor solutions way too often.
* Featured In Built In *
No-code tools have quickly become powerful building blocks for both technical and non-technical creators alike.
* Featured In Inc. Magazine *
Undervaluing a product or service is a common startup pricing mistake. So here are four pricing rules I run every new business through.
* Featured In Inc. Magazine *
Startup growth is an ongoing process that requires accessing both sides of your "startup brain." Here's a process to get you on the road to scalable growth.
* Featured In Inc. Magazine *
For a startup to afford great talent, there must be tradeoffs to fill the money gaps on each side. The most valuable salary tradeoff isn't equity.
* Featured In Inc. Magazine *
Launching a new startup isn't about scraping together money, throwing an MVP at a market, and hoping it sticks. Experienced founders take these steps to move forward.
* Featured In Inc. Magazine *
Your startup has a great product. You've found product market fit. You've got customers - maybe a few, maybe a lot. But you don't have traction. Now what?
* Featured In Built In *
Best practices for approaching a big sales deal with a large customer or partner - including examples of how I did it right and wrong.
Five preventive steps that will put your startup in its best position to survive and thrive -- in both good and bad times.
* Featured In Inc. Magazine *
Use these startup selling tactics cautiously. They've worked wonders for me. And also gotten me into a lot of trouble.
Forget 'Learn to Code.' Learn to 'No-Code' Instead -- It's time to put critical and creative coding concepts ahead of syntax and rote memorization.
* Featured In Inc. Magazine *
Here's what I've learned about how to keep all that debt from pulling you under, from over 20 years running or working with dozens of startups.
When you're leading, building or executing, you need to be able to quickly record ideas and catalysts outside of a formal brainstorming session.
* Featured In Built In *
I have a really hard time getting to the point. And as an entrepreneur, it's the most damaging thing I do.
Here is what I've learned over 20 years as an entrepreneur and startup leader, making decisions to give my business its best chance for success.
* Featured In Built In *
When you solicit customer feedback, here are the questions and answers you need to be thinking about in order to build a healthy and prosperous relationship.
Failure can be a good thing. And while a lot of people talk about learning from failure, they never tell you how to do it.
* Featured In Inc. Magazine *
Hiring technical resources will not solve all of your startup's technical needs, so here are the seven reasons that convince me to bring on tech help.
* Featured In Built In *
How does startup innovation happen? Here's the creative process that I've used for over 20 years to build innovative products.
When startup rules are taken out of context, the damage can not only impact the startup, but also its customers, supporters, employees, and investors.
Entrepreneurs who are told that failure is a treasure chest full of valuable startup lessons are being sold a false - and sometimes self-fulfilling - bill of goods.
* Featured In Built In *
I'll give you all the right reasons for keeping your startup in Minimum Viable Product mode until it's ready to find product-market fit.
Here's how to devise your startup's onboarding and engagement plan to lead your customers to success and generate more revenue and longer lifetime value.
* Featured In Built In *
You can't start a business without a lot of money. The question no one ever answers is: How much? So let's talk about that, using understandable numbers.
If an entrepreneur isn't turning an idea into a solution, they run the risk of that idea taking their business down along with everyone who supported that idea.
* Featured In Built In *
It's difficult for startup founders to present a cohesive belief in the company to customers and investors. Here's why you shouldn't add a cofounder to add legitimacy.
These are strategic tools experienced entrepreneurs use at each milestone in the startup maturation cycle to take their idea through reality to viability to scalability.
* Featured In Built In *
It's time to personally reintegrate with the professional world and figure out how to operate in the new normal because there is opportunity everywhere.
* Featured In Index by Medium*
I've broken down the "trojan horse" sales strategy into components that any entrepreneur can implement, so startups can help their product sell itself into large enterprises.
* Featured In Built In *
Bad Minimum Viable Products (MVPs) get launched too early, overreach on functionality, treat customers like users, don't work, and don't sell. Here's how to avoid all of that.
A lot of marketplaces tend to stall out soon after they get a handful of customers. There is promise and potential in their platform, but they don't generate revenue.
Leaning on buzzwords to describe your startup does exactly the opposite of what it's intended to do. It doesn't inflate the value proposition, it buries it.
* Featured In Built In *
Regardless of your motivations to start a business, your success will be defined by being honest about those motivations and acting on those motivations.
Are you prepared to do whatever it takes to save your sinking business? And would you know where and how to begin running life-saving experiments?
* Featured In Built In *
Here are several automation best practices to help your startup land new subscription customers while keeping existing subscription customers.
When you're an entrepreneur, you're going to face people who doubt your idea, your product, and your company. Here's how to make them an ally.
* Featured In Built In *
Defining your perfect customer persona leads to product-market fit, which is the key to a startup's ability to build a lucrative customer base.
Advancements in technology are making it possible for any company to sell more product with fewer resources using time-tested sales techniques.
* Featured In Built In *
It's hard to argue against making customers happy, but if your company is making everyone happy, you've definitely stopped innovating.
A strong tech focus can lure us to lean on our startup's technology as the core value proposition of our product. This makes our sales process unproductive.
If your startup wants to launch a new product to a high level of customer engagement, you need to overpromise the features and overdeliver the results.
Entrepreneurs using modern no-code platforms don’t need to know anything about syntax. This seems like a small change, but it’s actually a pretty big deal.
* Featured In Built In *
When you're an entrepreneur, the idea is nowhere near as important as the execution. Here are the top reasons why you might not be executing successfully.
* Featured In Built In *
An easy way to kill a promising startup is to spend too much time perfecting the product. The other really good way is to launch a product that isn't perfect.
* Featured In Index by Medium *
You don't need a team of salespeople, but you need to know your product, and be able to make snap decisions about sales, revenue, and profit.
* Featured In Built In *
Here's how to strategically say no to tasks that either overload you or are way out of your scope of expertise, and why this important for career growth.
* Featured In Start It Up *
Here is the best way for a startup or a young company to add a larger-than-normal multiplier to revenue return on its limited resources.
* Featured In Built In *
It's never been easier to start a side hustle than it is right now. But can you turn your part-time gig into a sustainable, scalable business?
* Featured In Start It Up *
What happens to your team, your company, and your livelihood when a personal crisis takes you out of commission? Let's develop a plan for that.
* Featured In Index by Medium *
Before you advertise your startup or product, you'll need to know these four concepts and data points to make your advertising campaign successful.
* Featured In Start It Up *
When pitching your startup to investors, you need to tell a good story about your path to market success, but you also need to back up that story with real facts.
* Featured In BuiltIn *
Whenever a young person asks me how they can make a career out of being an entrepreneur, I try really hard not to disillusion them. But I feel like it’s my duty to warn them that being an entrepreneur is a terrible career choice.
* Featured In Index by Medium *
It's not enough for your pitch deck to show that venture capital investment will lead to revenue growth. These are the most damning investor questions I usually get.
This process will not only monetize your platform more quickly, it'll make both your customers and vendors more successful, which means they'll come back and bring others with them.
After spending a couple months down the rabbit hole of NFTs and digital assets, I can tell you there are realistic startup opportunities, but also some chicanery.
Building a product for a niche market is a mistake waiting to happen, one that disappears quickly after failing to get traction with its intended audience.
* Featured In BuiltIn *
What does a startup do with their resources once the product is built? Strengthen the infrastructure or build a better product? Here's how to prioritize.
Even experienced startup leaders can succumb to opportunity or desperation in a way that turns a risk-tolerant strategy into high-risk gambling.
A random "expert" review of your startup's product, deck, or website will get you exactly what you pay for, or worse. Here's what you should do instead.
* Featured In BuiltIn *
Here's how startup leaders can identify a broken sales process, why we keep overlooking it, and how to fix it.
Competitive protection in business is more than just keeping secrets and filing for patents. It's about playing chess while everyone else is playing checkers.
Here's what my making-money side has taught my accounting side. These are things every entrepreneur should get control over before they launch their next product.
* Featured In BuiltIn *
All it took for the r/wallstreetbets explosion was a story, a hook, a catalyst, and a viral spark. This mirrors the rise and fall of every viral-fueled startup.
A legitimate business coach can be a windfall, a bad one can wreck you. Let's talk startup coaching - what it is, when it's legit, and when it might not be.
Running a marketplace startup that monetizes someone else's product will always be a slippery slope. Growing the platform seems simple, but it's easy to fail.
Why does every metric in startup revolve around money? Because a sustainable startup isn't a successful startup. If your startup is surviving, it's actually slowly dying.
* Featured In BuiltIn *
The drive to find the next new thing is what guides us entrepreneurs. And sometimes that leads us to betting our entire startup on a mirage.
Here are the five questions about your product investors will need answered before they'll invest in your startup.
The lure of subscription pricing is the guarantee of recurring revenue for your startup. But converting a subscription customer isn't as simple as flipping a switch.
* Featured In TechCrunch *
Being pushed out hurts more than failure, because failure is your own fault. How startup leaders get forced out of the company they were instrumental in building.
Why venture capital investor pitch contests seem attractive, and some of the signs that maybe your startup isn't going to win its next funding round.
Success or failure of a new technology lives and dies on customer trust. And trust in a two-sided marketplace startup is only as valid as the trust in its vendors.
Two-Sided marketplace startups are fertile ground for disruption, but their success can only be sustained if they avoid some common mistakes.
There isn't one set of singular strategies that makes the difference between a startup's success and failure. You need to write your own playbook for your own success.
Despite a two-decades-long decline of traditional media, there's never been more content making more money for more startups than right now. Here's why.
Experienced entrepreneurs will tell you that startup growth should be a sawtooth line. Here's how to deal with the risks associated with those ups and downs.
While the startup idea matters, it's the execution of that idea that makes the difference between success and failure. Execution brings change, so be ready to reinvent.
* Featured In BuiltIn *
Freemium models seem like an easy way to get new customers to fall in love with your product. But freemium isn't for every startup. Here's why.
In its simplest form, positioning is an exercise to determine what, who, and where your startup is. And it results in a path that gets you to product-market fit.
* Featured In BuiltIn *
Here are seven reasons why your startup should never serve ads to paying customers. It's not just bad for your customers, it's bad for your business.
Ultimately, startups can live with boring and useful, because they can get past that. Flashy and useless is just a pretty picture of an impending failure.
If you're an entrepreneur and you want to build a substantial product or startup with no-code, you're going to have to think like a coder.
When a startup prices a new product, there are basically seven parts to the equation. It's critical to know these numbers before you whiteboard or brainstorm.
* Featured In BuiltIn *
Pricing a new product requires vision, balance, and timing. When a startup gets those things right, it doesn't matter how wrong you were initially.
Recurring revenue is the key to startup traction and scale. Here are five alternatives to subscription pricing that can encourage repeat business.
Mainstream acceptance of digital communication has resulted in several opportunities for startups -- more funding, more talent, more sales.
* Featured In BuiltIn *
A startup can build a successful product by listening to four important people. But these same four people can also lead your business to ruin.
It takes founders a while to understand what type of entrepreneur they are and how to make that work for their startup. Here are the 5 basic types.
* Featured In BuiltIn *
I distill my years of experience running a technical and product development firm to save your startup some headache and maybe even a ton of money.
From two-sided marketplaces to on-demand startup models, there's a lot of misunderstanding about how subscription pricing generates revenue and profit.
There is actionable insight into what a potentially successful startup company looks like. Here are the intangibles I've seen venture capital investors miss.
In 20 years of building products, I’ve seen too many companies underestimate the overwhelming nature of supporting their product or service.
* Featured In BuiltIn *
One of the worst mistakes a startup founder can make is believing that a business problem can be solved by bringing on a cofounder.
There are several ways for entrepreneurs and CEOs to figure out if they're going to invent the next big thing without having to build the actual product.
A successful MVP doesn't guarantee a successful product. I figured out how to prepare my Version 1.0 launch to give every product I build its best chance for success.
A lot of entrepreneurs view a pitch deck like a homework assignment. I used to, then I realized that what I was pitching wasn't a startup, but an investment.
* Featured In BuiltIn *
There's only one way for a two-sided service marketplace startup to succeed. The platform must transact and deliver the traditional service in an innovative way.
When a startup attempts to build a product business out of an existing service model, there will always be the lure of leaning on the service to bring in revenue.
* Featured In BuiltIn *
Rejecting product ideas is a necessary skill for any entrepreneur. Otherwise you could find yourself picking up pieces of what, on paper anyway, was a sure thing.
The more you can tailor your product’s user experience to the individual customer, the more valuable your product, the more sales come to you faster.
The No-code Movement is hot right now. But can an entrepreneur build an entire business, company, and product without writing any code?
In 20 years being an entrepreneur, I've learned that for a startup to sell a new product, repeatedly and sustainably, you have to refuse to twist the customer's arm.
* Featured In BuiltIn *
There are seven basic traps entrepreneurs need to avoid when outsourcing tech for their startup, from budgeting money to protecting intellectual property.
Where do you turn to create your growing startup's leadership team? Inside your company or outside? We'll answer this thorny and common question.
* Featured In Marker by Medium *
Here's a primer on what startup disruption really means. To make it abundantly clear, we'll get into why Blockbuster Video was so pervasive in the 1990s.
As an entrepreneur selling products for over 20 years, I've learned that there are several misconceptions about what a startup sales call should be.
There is one mistake that leads an entrepreneur to go from leaning on a metaphor to explain their startup to falling into the trap of actually living that metaphor.
Here's how a startup develops an effective Customer Success strategy, whether you're just getting started or you've already got a ton of customers using your product.
For a two-sided marketplace to get any traction, the platform has to match vendor strengths with customer needs. But this isn't as simple as it sounds.
When I'm building a business, I'm not relying on startup expertise, I'm relying on my startup experience. It may seem like a trivial difference. It's not.
* Featured In BuiltIn AND Marker *
It's critical that you monitor the health of your startup, but you don't have to spend a fortune on custom solutions or business intelligence systems, yet.
Why do startups make splashy announcements at launch? Because that's the way it's always been done. But that strategy can actually backfire.
* Featured In BuiltIn *
Everyone tells you to build what your customers want. Here's how to establish a customer-driven build process without drowning your startup in complexity.
To successfully land outside investment for your startup, you'll need to avoid a few misconceptions about how startup investors operate.
* Featured In BuiltIn *
When you use subscription pricing, your startup must reshape your offering to conform to a model that not only generates revenue, but profits as well.
Here’s how to make outsourced hires work for your startup, across all roles, and no matter what stage your company is in.
* Featured In BuiltIn *
If you can build your startup to viability, you have everything you need to create traction and scale the business.
Startup founders and business leaders oftentimes put too much trust in data, which can quickly become a problem that manifests itself in sneaky ways.
If your startup gets into the habit of always giving your customers what they want, you might be on a slow road to failure. Here's how to detect and avoid that trap.
For a business to survive and successfully thrive, it has to grow. But most entrepreneurs doom themselves by mistaking rapid growth for high-growth.
As leaders of our startups, we need to be proactive about managing stress in our workplace before issues arise. Here are some steps you can take.
* Featured In BuiltIn *
How startups can create efficient marketing funnels, and how to find and sell to people who will be just as passionate about your product as you are.
* Featured In Entrepreneur's Handbook *
Scaling a business isn't rocket science. Here's a 6-point plan to help any type of startup accelerate revenue growth using data and technology.
Here are the steps I've learned to get from viable solution to high-growth company, based on over 20 years building and advising high-growth startups.
One of the lessons I've learned in 20+ years as an entrepreneur is that there are good reasons to launch a product that's not quite ready. Here are those reasons.
* Featured In BuiltIn *
For a startup to successfully bring an MVP to market, instead of telling your customers what you are, you need to focus on who they are. Here's how.
The only scenario that leads to a startup not being able to choose its acquirer is the one where the founder never thinks about who that acquirer should be.
When a startup launches a new product, it faces a unique marketing challenge. The messaging not only has to sell the customer, it first has to educate the customer.
* Featured In BuiltIn *
Startup success can hinge on a useful minimum viable product. Here's a four-step plan for building an MVP that shows value to the customer immediately.
An entrepreneur should be a grinder, not a gambler, because startup isn't about the once-in-a-lifetime idea, it's about a lifetime of ideas.
* Featured In BuiltIn *
For two-sided marketplaces to succeed, the platform has to add value for both the customer and the vendor. This is especially critical for Expert Marketplaces.
Everyone says you need to fail at startup. Very rarely do they tell you why failure is important and how the seeds of failure become of roots of success.
Customer success makes sure the customer gets maximum value out of the product, and also makes sure the product gets maximum value out of the customer.
Great products are usually built from ideas that seem crazy at the time. But with constant ideation, what starts out as laughable can turn into something amazing.
* Featured In BuiltIn *
Two-sided marketplaces are often lacking. The matching is usually poor, the transaction isn't timely and, worst of all, the experts aren't really experts.
A startup is no ticket out of the real world. There's no escaping malfeasance, manipulation and straight up evil. So is your company a utopia or a dystopia?
* Featured In BuiltIn *
Most companies spend a lot of time thinking about customer service. Very few companies spend time removing customer friction. Here are some ways to do that.
* Featured In BuiltIn *
An explanation of what an expert two-sided service marketplace is, why these marketplaces are becoming mainstream, and the issues that lead to their failure.
Entrepreneurs spend an inordinate amount of time chasing down opportunities that never materialize. Here are some strategies for when, why, and how to say no.
* Featured In BuiltIn *
There’s a lot of talk about whether or not investors are still writing checks to startups during the pandemic. The problem is no one knows anything yet.
Our entire world got blindsided going in to the pandemic and the resulting crisis. Let's make sure we don't make the same mistakes on the way out.
Leadership training isn't new, but it's suddenly hot. Is it valid? Is there an ROI? How do you choose a trainer? Here's how to figure that out.
* Featured In BuiltIn *
Free product strategy is changing, but there's still a requirement of countermeasures to benefit your business on the back end. Here's what those are.
A look at why service subscription pricing makes so much sense in this new normal for business, along with guidelines for how to create the models.
A cautionary tale about starting a business with the wrong people, and what to do if it's already too late.
* Featured In BuiltIn *
Is the door closing on your job really a window opening on entrepreneurial opportunity? There's actually a pretty easy answer for this. You just need a plan. Here are three.
We need to be able to work through panic and through big deal events. The overwhelming reaction from your brain and your body will be a desire to shut down and sink into it. Now is not the time for that.
* A Medium Editorial Feature *
Every startup - from inception all the way through to the last pre-IPO funding round - has three defining stories. It's up to company leadership to sell these stories to customers, investors, the team and themselves.
* Featured In BuiltIn *
A checklist of when, how, and what to ask your customers to get the most useful feedback with the least amount of friction.
If a startup isn't growing, it's dying. So you should be thinking, planning, and acting in growth mode all the time. Here's how to transition your company up and out of the muck.
A company having two CEOs can work. In fact, there is a time in a company’s life cycle when it works extremely well; in the growth stage of a startup, having two leaders is almost necessary.
* A Medium Editorial Feature *
Increase your chances of a successful product launch by creating an MVP playbook, a living document that dictates how a product is delivered, executed, and supported.
For most startups, custom development is expensive. On top of that, the choices are confusing, sometimes arcane, and constantly changing.
People hate change. But some people just plain love the freaking status quo. What do you do when these people are your potential customers?
A startup exit is awesome if you can survive the grind. And that can be easier said than done. Wait for the exit or jump ship? Here's what you need to ask yourself.
When you’re running a startup, it really is you against the world. But while being the underdog can be a huge source of motivation, the fact that you’re never on a level playing field can wear on you over time.
I believe that every company needs some degree of skunk works within its walls, at all times. It's something I've done with every single startup I've founded or been a part of, and I'll share with you the ways I've seen it work.
Being a cofounder is about more than just being there at the beginning. And handing someone the wrong role can turn into a costly mistake. Let's talk about how to avoid that.
Every startup founder faces an overload of critical decisions early in the life of their company. None of these decisions are more important than selecting the first few people you choose to work with.
Early in my entrepreneurial career, I got really good at the elevator pitch - a collection of word salad that purports to highlight the most valuable aspects of a startup idea in 60 seconds. In fact, I peaked at mastering the elevator pitch right before I realized the utter uselessness of mastering an elevator pitch.
I'll give you the bad news first. When you're the founder of a growing company, at some point you're probably going to lose control of your board.
* A Medium Editorial Feature *
I still take too many meetings. Even after 20 years in the business of being an entrepreneur, I still wind up booking at least one useless meeting a month.
* A Medium Editorial Feature *
The role of a startup advisor, or for that matter, any business advisor, is often misunderstood, even by those would-be advisors themselves.
* A Medium Editorial Feature *
A lot of great startup advice comes directly from parenting. And if I were the kind of parent who gave parenting advice, a lot of my parenting advice would probably come from startup.
Here's the Catch-22 about experimentation. It kills your revenue, your customer reputation, your employee morale, and your business rhythm. But if you don't experiment, all those things will wither and die anyway.
* A Medium Editorial Feature *
I get tons of inbound from entrepreneurs and founders, from first-timers with an idea to CEOs with millions in annual revenue, and they all ask what basically boils down to the same question: "I've taken my startup this far, how do I get the money to take it to the next level?"
* Featured in TechCrunch *
Let me ask you a strategic question. Where do you want your company to be three years from now? What will your product or service look like? Which new features will you roll out and how will your business evolve?
* A Medium Editorial Feature *
Nobody likes hardware startups. Investors can't run away from them fast enough, customers are always hyper-skeptical, and retailers love inventing new hoops for new products to jump through.
* A Medium Editorial Feature *
Last week, one of the founders I'm advising landed a lucrative and potentially game-changing customer. This was a moment of truth in more ways than one.
* A Medium Editorial Feature *
If I gave you unlimited funds, time, and talent, could you build a wildly successful product? Wait. Stop. It’s a trick question. None of those things actually matter. As recently as a few years ago, a startup could get away with hiring a crack development team to build a product from the ground up, based solely on a good idea.
No matter what your startup is selling or who you're selling it to, in order to survive, you'll need big customers and you'll need lots of them. But how do you land million-dollar deals with limited resources and no credibility?
* Featured in TechCrunch *
Last year, around this same time, I committed to writing two startup advice posts a week on Medium. I started on January 2nd, 2019 and this will be the next to last one for the year.
In the hundred or so startup advice posts I've written this year, my secret is that I'm not trying to advise you to start a company, or join a startup, or invent something world-changing. I just want you to understand that no matter what you do, where you do it, or who you do it for, you still have the time, the talent, and the resources to become exactly who you were meant to be.
A partnership with an existing business can be a huge win for a startup. But just because a bigger, shinier company wants to be your new BFF, it doesn't mean the revenue firehose is going to be aimed your way.
These days, it seems like anyone can stitch together a simple two-sided marketplace. All it takes is using readily-available technology to gather a big group of customers on one side and a curated list of providers on the other.
* A Medium Editorial Feature *
Each service business is unique and comes with its own problems and limitations. So here's my advice to the hundreds of you who have written in and the (probably) thousands more who haven't.
Should you be slow to fire or quick to fire in the early days? It's a tricky question and the right answer depends on some thorny subjects. So let's talk through it.
* A Medium Editorial Feature *
Whether you're a founder or you just have some equity, there's a bunch of stuff you need to know before you decide to sell your startup, stuff that you won't actually learn until you've been through it.
* Featured in TechCrunch *
Every entrepreneur will arrive at a crossroads where we can do the right thing and lose or do the wrong thing and win. If that kind of win never sits right with you, read on.
Let me ask you a question, and think about it for a second before you answer: Have you ever been totally bored and completely stressed out at the same time? Right? Me too. It's actually pretty common in startup leadership circles but no one ever realizes it until someone asks them the direct question.
* A Medium Editorial Feature *
Let's clear up a common revenue misconception right away. Choosing a revenue stream and settling on pricing are two completely different exercises. The latter is what our customers are going to pay. The former, and what I want to talk about in this post, is what our customers are paying for.
Intrapreneurship is not new. As a big company concept, it's been talked up for decades, because the lure of entrepreneurial strategy mashed up with the seemingly infinite resources of an established player is super enticing for both sides.
* A Medium Editorial Feature *
Let me ask you a question that needs an honest answer. Do you want to be rich? Because your answer might dictate what kind of startup you're building.
The hardest role to fill in any company is leadership. Say what you will about logic-defying compensation packages and golden parachutes for C-level executives, because I'll nod my head right along with you. The hard truth is that experienced leadership is always the difference between success and failure. Always.
If you want to acquire more customers, you have to satisfy more customer needs. Oh, and you have to do it without asking what those needs might be. And finally, those needs will change, probably from day to day.
You're probably hearing the term "company culture" more often and in broader context. Culture is no longer the domain of progressive West Coast startups and forward-thinking Chief People Officers. At some point over the last five years or so, shit got real.
Marketing an MVP is almost like reinventing the wheel every time out, and every plan is as unique as the product it’s selling. But if you stick with these overarching rules, you’ll be able to design a marketing plan for your MVP that gets results you can build from when it’s time to market the real thing.
If you're thinking about raising money to fund your startup, you need to take a hard look at corporate investment.
Let's talk about whether or not you can determine a startup will be a success before it actually brings in any money. Because while there's no good way to do that, there are some cheats.
At some point, every startup will have at least one employee who threatens the success of the company. What do you do with this person?
Since the beginning of 2019, I've written several posts about the concept of Minimum Viable Product, everything from what an MVP is for and how to do it to what you can expect to learn from it.
If you're going to ditch your day job and step out on your own, you're going to want you to make sure that what you're stepping into evolves into a sustainable, profitable, and growing company.
Let's talk about why you haven't launched your product yet, and how you can get it to market today.
I've founded, worked at, and advised a ton of startups, and each one tends to make the same mistakes where revenue is concerned. Whether a founder is launching their first company or their fifth, there's one universal fact they can't ignore: The path to success starts with survival.
* Featured in Business Insider *
Let's talk about the damage being done to your company by customers who aren't actually paying customers.
There are tons of lessons to take away from Wag's story, most of them about how not to build a service marketplace. Here are the major lessons I found and what you can learn from them.
Every innovator has an idea of what the successful version of their product will look like. But one of the failings of a typical MVP is that it usually results in more questions than answers.
Some entrepreneurs spend way too much time worried about the endgame. Others get an acquisition offer dumped into their laps and have no idea what to do next.
* A Medium Definitive Guide *
It's no secret that a product company is much more valuable than a service company. It's why every service provider has that dream about transforming their service into a product. The problem is that there are a lot of wrong ways to put that evolution into motion, and doing it wrong can kill the business pretty quickly.
Let's talk about crafting the perfect investor update. And more importantly, how to get them to respond. Every startup is different, and there is no single template for an investor update email. But I've learned that there are a few rules that you have to follow to get them to read it.
Your business can grow or it can remain profitable. Doing both at the same time is a circus-level juggling act. But it can be done.
* A Medium Editorial Feature *
Let's talk about who your best customer is, because it isn't you. Of course, I'm not saying that startups shouldn't use their own product. We absolutely should. But regardless of how familiar we are with the problem or how experienced we are with the market, when we're the creator of the solution, we tend to turn into a terrible customer.
No good investment is ever made without a relationship already in place. No good relationship ever starts out by asking someone for money.
Let's talk about how we build a product from scratch with low technology and no code. Not just a mock-up, but an actual product we launch, sell, and grow.
One of the most underrated secrets of success in startup is the ability to build not just a great product, but a great company.
* A Medium Editorial Feature *
There are a million challenges when starting a business, and one of the earliest is finding the funding to get your business off the ground.
* A Medium Editorial Feature *
A lot of people, including me, talk about when to launch an MVP. Let’s talk about when we shouldn’t. Chain reactions from one big mistake can take down great ideas, strong teams, and solid companies.
One of the coldest truths about startup is that it's pretty freaking lonely. I don't mean lonely in the sense that we spend long days in front of flickering laptop screens in dark, windowless basements. No, in that sense, startup is actually kind of social. When I say startup is lonely, I mean there aren't a lot of places to turn when we feel like we're going it alone.
What exactly does your product do? This is the most challenging and brain-bending question a startup faces, because if a Minimum Viable Product (MVP) is going to succeed, its description has to be deceptively simple. And by "deceptively," I mean it has to convey a ridiculously complex idea in about 15 words.
Have you pivoted lately? If not, you should probably be thinking about it. Yes, a proactive pivot. Why? Because you’ve heard that old phrase: In startup, if you’re not growing, you’re dying. A lesser known but more actionable phrase is: If you’re not changing, you’re not growing.
I'm seeing a growing epidemic of startups built off surefire business school concepts and buzzword-heavy strategies. I've got three recent examples of startups who reached out to me - they did everything they were supposed to do, everything they were told to do, and yet they still flamed out. There's a common thread between all three: They all started with a really good plan.
If you're going to do startup, you're eventually going to fail. It will be shocking, painful, and costly. And until you've failed a few times, you won't be ready for it, because failure is one of the most misunderstood topics in startup. Let's fix that.
Let’s talk about how we turn an audience into a customer base. And let’s start with how we don’t. Here’s how we break down who they are and what they need, how we sell them our MVP, and what we can learn from each of them.
Let’s talk about why entrepreneurs have a mandate to take giant risks and make crazy decisions. If you read me regularly, you might get the sense that startup is a numbers game. And when I say “numbers,” you might think that I mean money.
In startup, the difference between survival and running out of runway always comes down to taking our eyes off revenue. We don’t want to do this, and we certainly don’t do it on purpose. But when we’re in the middle of the startup run, it’s pretty easy to fall into a trap of wasting our time on feelgood tasks that seem like progress but don’t bring in any money.
* A Medium Editorial Feature *
Let’s talk about how pricing models can help build a relationship with your customers. Your product isn’t just a product. More often than not, it defines the relationship between your company and your customer.
Much of what you hear about the work habits of millennials isn’t always true, but one trend is becoming increasingly clear: They don’t want their parents’ career.
Working for free is a common practice and even a necessary one at that. Most truly new ideas need true believers to get them into an executable state, let alone a revenue generating state. That only becomes a problem when we start asking others to share that risk, especially those folks who aren’t co-founders.
One of the biggest mistakes entrepreneurs make is trying to be a competitor in an existing market instead of creating their own market. In this post, I’ll give you some case studies and strategies to get you thinking bigger.
One of the most common questions I get from company leaders is about who to hire and when. It doesn’t matter if your company is two people or 20 or 200, your next hire is always the most important hire. Filling the wrong role at the wrong time is a waste of money and potentially even a waste of talent.
* A Medium Editorial Feature *
If an organization isn’t using data to develop and grow its products, then its days are probably numbered. Let’s fix that, because every new product, every new feature, every growth experiment, should be using data to make decisions.
Most of us entrepreneurs chase success like a dog chases a car - we don't know what to do with it when we catch it. That's because most of us have at least one weakness in our growth game.
There is no better professional achievement than launching a product and watching it succeed. But a successful product launch is really nothing more than a glorified proof of concept. No company ever survived on the hype of a launch, no matter how high the trajectory of the rocket. Once that rocket is up in the air, we lose a lot of control over it, and the period immediately following the launch is often marked by total chaos. What we need is something that looks more like organized chaos, and for that, we need a product team.
I need to ask you a sensitive question. How many times have you gotten screwed out of fair payment for your product or service? If the answer is more than “zero,” then you’ve probably made sure it’ll never happen again. Right? Or have you? Chances are, there might still be gaping holes in your payment strategy.
If we’re going to spend time on competitive analysis — and mind you, lack of competitive awareness is one of the top reasons investors reject growth stage startups — we might as well go all in. Here’s how to do just that.
Customer indifference is the number one killer of new products and services. It can be tricky problem to solve and even more difficult to detect, because it’s often mistaken for something else.
Launching a successful Minimum Viable Product is only the beginning. Selling and scaling an MVP is harder and riskier. If our product doesn’t emerge from MVP and quickly generate enough revenue to push our startup into the growth phase, our startup will stagnate. However, there are a couple challenges we’ll face right out of the MVP gate.
There’s a right way to approach crowdfunding, and a whole lot of wrong ways. Some of those wrong ways could lead to litigious customers, fines, and even criminal charges. So let’s talk about avoiding the most common mistakes entrepreneurs make when considering crowdfunding.
It’s easy for an entrepreneur, new or experienced, to fall into a loop where we freeze on decisions, second-guess ourselves, and get overwhelmed trying to map out the next steps of our company’s progress. At these points, we need help, experienced help, and we’re not sure where to turn.
In business, your leverage in negotiations is directly proportional to your size. When you're a startup, you're freaking tiny. So how do you get a deal done without giving away the company?
A startup has to get its pricing right or the product will be dead at launch. The problem is, there aren’t a lot of hard and fast rules for pricing a brand new product. Having launched dozens of digital, physical, and hybrid products to market, I’ve developed a few general guidelines that have worked for me when pricing an MVP.
A startup has to get its pricing right or the product will be dead at launch. The problem is, there aren’t a lot of hard and fast rules for pricing a brand new product. Having launched dozens of digital, physical, and hybrid products to market, I’ve developed a few general guidelines that have worked for me when pricing an MVP.
It doesn’t matter if it’s our first startup experience or our eleventh, the skills we need to master to get from where we are to where we want to be, they don’t really change. So here are those things we need to master to rise up through the startup ranks.
Startup burnout is a real thing. As the stigma traditionally associated with mental health issues melts away, we’re seeing a lot more entrepreneurs and startup employees raise their hands when the stress levels get too high.
Startups are founded on the premise of disruption, and the tech we use to facilitate that disruption likely has multiple efficiencies coded into it that can be reapplied to other use cases. This is where the crazy money is made, because it can elevate our company from niche product player to new market dominator.
To succeed in startup, you not only have to land the best talent, but you have to land and keep the best talent at the most value. Here’s how you do that, with four secrets no one else might tell you.
Entrepreneurs and investors are placing bets that the gig economy is about to normalize and become an even greater share of the real economy. Here’s what I’ve learned about building the basics of a gig market platform MVP.
Let’s talk about fallback strategies for when your biggest customer breaks up with you. I’ll prescribe a fix, but more importantly, I’ll lay out a strategy for prevention.
Listen up. If your company is being acquired, or if you’re planning for an acquisition as your exit, you need to know what’s coming. Because a lot of it isn’t pretty.
Good entrepreneurs worry so much about where the next customer is going to come from that we never think twice about whether we should take on, or keep, a customer that's more trouble than they're worth.
* Featured in TechCrunch *
Making a mistake launching a new product feature is costly, and I’ve done it at least a dozen times. Never again. We’re all familiar with the Minimum Viable Product (MVP) strategy. What’s gaining traction now is the strategy of repeating the MVP process with every new feature, even down to every new version. How do we do that?
If we’re starting a company that we hope will one day reach a billion dollar valuation or more, we’ll need a different kind of strategy from the beginning.
Let’s talk about when we need to start paying the true believers working for our startup. With actual dollars. Because the alternative is usually promises. And promises in startup are always a bridge built to burn.
At what point does a founding CEO grow the company beyond their ability to grow it even more? It sounds like a Catch-22 of a question, but it’s a standard move that I believe startups get wrong more often than not.
As entrepreneurs, it’s almost impossible to understand the value of what we’re building, and there are several reasons why we’ll sell our product for less than what it’s worth. Let's overcome that.
* A Medium Editorial Feature *
Every entrepreneur comes up with simple sales targets soon after figuring out their most basic price point. We can’t help it, it’s what we do. But when it comes time for real sales projections, the math gets murkier. And we’re usually still just throwing random numbers at a wall and hoping they stick.
Ask anyone who’s been there more than once, and they’ll tell you. Right at about 50 employees is where young companies start to go off the rails. So what should we do when it happens?
* A Medium Editorial Feature *
Let's talk about how we use data to make a better product, raise our margins, and generate more revenue. Here's a really quick way to make sure we're building a strong, robust product that our customers want.
Last week, I got a bunch of questions via my website from “Devin,” a smart young entrepreneur in the healthcare technology space. His MVP, a mobile app, was about six months from completion before he realized he needed to do more work around his business concept. Now his MVP is about a year out, and he’s frustrated because he wants to reach out to his target market to gauge interest in his solution.
You know how startups can one day just suddenly implode, leaving a well-meaning but ultimately hollow note on their website thanking everyone for the incredible journey? It hurts every time I see that. Because you can prevent it. Not all the time. But you can see it coming. All the time.
The role of “product” within almost all industries is trending toward less emphasis on product management and product marketing, and more towards using technology and data to determine everything from what we’re building to how we’re selling it.
Firing an employee, especially at the startup level, is hands-down the toughest responsibility a founder or executive has to take on. I know this sounds like an elitist problem — oh, it must be real rough to have to ruin someone’s life. It is. Unless you’re an a-hole.
* A Medium Editorial Feature *
When I see a working product not selling, it’s usually because the value premise was off from the beginning. What it almost always comes down to is: Does the product have a traceable direct value for the customer?
Let’s talk about how we deliver software when it’s ready, instead of when it’s due. This is how I’m transitioning from promising and missing dates to delivering continuous innovation, both across my org and to my customers.
The harsh economics of startup are often easily overlooked. So let’s talk about what it really costs an entrepreneur to get a startup off the ground. It’s about 250 grand.
Last week, I had an email exchange that came through my website from a college student who sort of lucked into a startup founded by one of his friends. He had jumped in at the beginning, and now he's at a crossroads.
I live by the entrepreneur’s motto: “It’s easier to ask forgiveness than to get permission. But it actually matters what you’re going to ask permission or beg forgiveness for.”
At some point, every entrepreneur stops innovating. Let’s talk about how to put that off for as long as possible.
Your MVP is your first impression, both for your startup and for you as an entrepreneur. Here's a high-level checklist I use to give my MVP its best chance, with some real-world examples thrown in.
Should you learn to code? I used to always answer with an emphatic yes. Now I’m like 80/20 no. The catch is, and always will be: Time. Here's how to get around that.
Building software under a deadline is a recipe for disaster, right? So why are we still doing it? It’s not gonna be too long before we look back and laugh at when we used to put delivery dates on tech.
Leadership flaws can start tearing at the seams of a startup right at the first signs of success. If we don’t have leadership that works, we can’t make critical decisions, we can’t move forward, chaos ensues, and the whole operation begins to crumble from the top down.
When you’ve been an entrepreneur for as long as I have, you have a million ideas. Granted, a lot of these are trash. You can’t get to the great ideas until you sift through all the crap ones.
I used to hate the Beastie Boys. And I put that half on me and half on them. I was a kid when Licensed to Ill came out of nowhere and was suddenly everywhere. But I wasn’t just any kind of kid, I was a rock snob. A douchey rock snob. That’s on me.
An MVP is indeed meant to be the quickest version of the product you can put out to market. But when I use the word “quickest” here, that reduction in time to market is achieved by a reduction in feature set, not a reduction in quality. Lately, I’m seeing the pendulum swing away from quality too often.
What would you say your company does? It seems like a simple question that should have a simple answer, but that’s rarely the case.
Through the lens of common elements like startup, career, technology, I’m really trying to communicate a higher level of thinking when we think about what we do. And in that, I’m really just hoping to make people’s lives better.
In a 20-year career as an entrepreneur, I’ve been lucky enough to have a few wins. But I’ve also had my share of startup failures, and I learned more with those than I did with the successes.
I’ll walk through each of my five startup acquisitions, and pick one thing I should have done differently, either before, during, and after.
Artificial Intelligence gets a bad rap. The science of AI and machine learning is solid, defensible, and utterly useful. It’s how we’re applying that science that rarely makes any sense.
The worst kind of startup isn’t the one that fails, it’s the one that stagnates. In startup and small business, if you’re not growing, you’re dying.
A couple years ago, in a perfect storm of circumstances, I wound up selling two companies nearly back-to-back. Here’s my story and, now that I have hindsight, what I learned.
One of the toughest questions I get about startup happens to also be one that I get the most often: How much of a pay cut should I expect to go to work for a startup?
As a career entrepreneur, I wear the customer-first badge. Proudly. I strongly believe raising money through customer sales is the best option, and in a lot of cases, it should be the only option.