“Do you want to be rich or the perpetual king/queen?” That’s a question an investor might ask a first-time founding CEO. What they’re trying to determine is if the founder…

The puzzled look on a first-time founder’s face after hearing an investor’s concern of a “messy cap table” happens more than some probably think.  But what the heck does “messy”…

Service companies traditionally have low gross profit margins as compared to tech companies, especially software. That’s because services require human bodies to deliver most of what the customers are paying…

In the very early days, many startup founders get legal help from a relative or college friend that also happens to be an attorney. But if they aren’t a corporate…

Founders of hardware startups quickly get tired of hearing the phrase “hardware is hard”, especially when voiced from someone that has never worked for a hardware company and has very…

For much of my career, a one-hour meeting was the norm.  But in the world of startups, 30 minutes is all you get most of the time for sessions with…

Somewhere along the way, you and your co-founders will be faced with the need to hire your first employees.  Regardless of how much funding you have for salaries (versus equity…

I regularly get introduced to a career corporate execs that has an interest in mentoring or advising startups. Oftentimes, it is because the executive recently retired or is planning to…

Understanding the post-termination exercise period for stock options is crucial for tech startup founders, advisors, board directors and early-stage venture investors. In this comprehensive guide, you’ll gain valuable insights into…

Upon a startup’s incorporation, their attorney usually helps establish a board of directors (aka – the “board”), even if a solo founder is the only board member.  The company’s bylaws…

I regularly hear startup founders longing for the day when they reach $1 million in annual revenue. They proclaim how much easier everything will then be. But I also regularly…

It royally sucks when a founding team reaches a point where they decide they can no longer work together. This is especially true after a year or more of really…

Just from the article’s title you probably think you know everything I’m going to say, right?  I predict not but soon we will find out.  The basics definitions of aspirations,…

How many times have you read about a rocket ship company that’s taking over the world?  You get green with envy after imagining what it would be like to sit…

After deciding your new business venture seems worth pursuing, you will have quite a few decisions to make regarding incorporating your new entity.  You might decide to read online articles…

In the earliest days of a startup, the founders are hugely optimistic and driven.  But they also know about the low odds of reaching the point of having paying customers…

It’s amazing how often I ask an entrepreneur to tell me about the business they are building only to get a response that goes on and on about the product…

While in the coffee shop with your co-founder and blank sheets of paper for brainstorming you are in what I refer to as the “hope, vision, promise and potential” phase. …

A company founder has no choice but to secure the first sales of their newly-created product and the first strategic partnership.  That’s because they can’t afford to hire a sales…

Successful emergency room doctors must be highly intelligent and calm under pressure.  Successful  triathletes must to be goal-oriented and driven.  Successful songwriters must be creative.  What about entrepreneurs?  Entrepreneurship is…

When I ask entrepreneurs what their most valuable resource is, I ALWAYS get one of two responses: money (aka – funding, cash) or people.  And it’s hard to argue about…

What do buying a new smartphone and being given a gift card have in common?  In both cases you want to extract value as soon as possible.  With the gift…

It seems like everywhere you look now there is some form of startup program advertising their method of helping entrepreneurs increase their odds of success.  From incubators and accelerators to…

Online marketplaces are being created for just about anything you can think of.  Some have a local services component on one side of the marketplace that carries an extra burden…

Many (probably most) startups go through periods of extremely little cash in the bank and with visions of crashing and burning before being able to recover.  Unfortunately, crashing and burning…

How can something that’s free and openly available cause so much unintended harm to your business?  The availability of open source software has contributed as much to lowering the cost…

When you first incorporated as a C-corporation, probably only you and your co-founder were named as board members. You never really had official meetings or voted on anything, that you…

I know what you’re thinking.  “We don’t even have 20 employees, so why do we need a management system?”  You might be thinking this because you previously worked for a…

If you aspire to build a company that is scalable, then the size of your market is a very important element of your business plan. That’s because it suggests the…

You see it all the time.  A young, invincible hacker-hustler duo join together as startup co-founders to pursue a dream of becoming the next Google or Facebook.  The hustler takes the CEO…

In the earliest days of a startup venture, there are no published compensation rates or even good studies to use as guidance.  That’s because each company and founder situation is…

I get the following question all the time from US-based startups: how should we price our individual units of equity? (shares of stock for C-corps; units for LLC’s)  It’s a…

It’s amazing how quickly legal costs can add up. If you’re running a startup, it’s possible that your legal costs are second or third highest amongst all of your expenses....

If you already have an experienced product manager on your team, they are probably/hopefully following some well-established product management process. But what about the early days of company formation before…

Throughout your startup’s evolution you’ll find that you do a lot of networking with others that can potentially help you.  This includes potential business partners, employees, advisors, angel investors and VC’s.  Regardless…

You’ve just completed a great investor pitch with heads nodding and good interaction.  You’re about to ask “Does this opportunity interest you enough to explore an investment?” when instead you get…

Similar to the “So What” rule, every time you make a claim, prediction or forecast, imagine your audience is thinking to themselves “yeah, right!” in skeptical fashion immediately after seeing/hearing your…

Once you have a product in the market with an increasing number of paying customers, your valuation will increasingly be driven based on financial and operational metrics.  Don’t get me…

It’s not innovation or company culture or a determination to win.  Those are all important but successful big companies have at least some of those things too.  Startups often have…

The title of this article suggests you’ve already decided that you need one or more advisors.  But spend time with your co-founders discussing this to make sure you agree it…

How much equity should you give to compensate an advisor?  Should the shares carry any special provisions like anti-dilution or change-of-control acceleration?  What about giving the advisor cash compensation?  Tough…

Startups commonly give 0.5% equity or more to attract an experienced advisor (see related article titled “Compensating an Advisor”).  Sometimes after a few months they find themselves wondering if they…

There’s a reason it’s referred to as an “elevator pitch” – it must be expressed in a few sentences and no more than 15-20 seconds.  And that might even be…

I’m afraid the current “don’t waste time creating a business plan” mantra is doing unintended damage.  It’s leaving the impression on first-time entrepreneurs that they don’t need a plan of…

If you’ve seen my bio or LinkedIn profile, you’ll know I’ve served three stints as a CMO and roughly half of my professional career has been spent in a marketing…

I guess the corollary to this could be “don’t use a compass when the precision of a GPS is needed”.  In fact, the main point is to use the best…

I don’t have anything against a traditional SWOT analysis but recently found myself helping a couple of startups figure out how they are progressing against their business plan and vision. …

Too many startups discover they’ve got an acquisition-blocking or acquisition-inhibiting issue after a price tag has already been agreed with the acquirer.  It comes out during due diligence and the…

It’s unbelievable how many startups get into trouble not because they aren’t finding product-market fit or because their customer acquisition model is inefficient but rather because the co-founders have some…

It happens over and over and over again.  A company has a successful growth spurt and is ready to ratchet up to the next level.  They are sitting around a…