I'm A Smart Bear (Jason Cohen), founder of 2 unicorns, both bootstrapped & funded; bought, sold, and invested in startups. AMA!

I built several companies over the past 23 years:

  • ITWatchDogs – bootstrapped with co-founder; server-room climate and power monitoring and altering using hardware + embedded software; sold in 2004 and still selling its products today)
  • Smart Bear – bootstrapped as sole founder to millions in annual profit; software for peer code reviews before it was cool, invented the modern methods and wrote a book about it; sold in 2007, left in 2009, it continued to grow and is now a unicorn.
  • WP Engine – initially bootstrapped but raised from VC 2 years in, eventually $300M raised, even more in ARR; one of the largest public website platforms on Earth, platform and developer tools for making WordPress sites. 13 years in, 200,000 customers, 1200 employees, still growing and profitable.

I’ve been writing about startups for 16 years: https://longform.asmartbear.com; between that and some now-classic talks and Twitter, that’s how most people know me.

I’m happy to talk about anything whatsoever, but here’s some topics where I have a lot of ideas and experience:

  • Strategy, especially practical non-academic strategy, at any scale
  • Product, at any scale
  • Engineering challenges specifically due to scale
  • Bootstrapping vs Fundraising
  • Company culture/values – creating and inculcating, at first and at scale
  • Management / organization for people who haven’t done it before, and maybe even hate it
  • Role of the CEO and other executive positions as the company grows
  • Metrics/KPIs, whether operational or “SaaS” or how to figure out good ones
  • Managing your own turmoil, emotions, grit, dispare.

I’ll be back on June 22nd, 11 AM US Central Time (4 PM GMT) to answer questions.

Looking forward to this!


This June 22nd, we’re incredibly excited to be hosting WP Engine’s founder, Jason Cohen. Who, as an ardent, discerning practitioner-chronicler, has made the most unyielding SaaS/startup subjects vividly accessible. From revisiting standard industry practices (“‘MVPs’ are too M to be V’) to reexamining individual causes of burnout (“what creates a fulfilling existence?”), Jason has experienced, and rigorously, evocatively, admirably documented it all.

Jason Cohen’s brain-pickings :brain:

(Curated excerpts to give you a sense of some of his beliefs and thought processes)

On questioning the long-held advantages of being first:

Most startups insist they’re “first” at something. As they should — what’s the point of a new company that adds nothing new to the world? But is it a good thing? Does it make you better than your competition?

On the surface being “first” sounds impressive, implying innovation and leadership. But upon reflection, it’s not.

In fact, being first is a shackle because you’re stuck with legacy support — features you thought were important but aren’t now, grandfathered customers who are no longer profitable, and a reputation that’s hard to revamp even if your company has in fact changed.

Worse, being first means you make all the mistakes in public, for all to see. New competitors get to swoop in afterwards with the hindsight that you created — in pricing, positioning, marketing, features, design, … anything. They get the running start without all your baggage.

Of course there are situations where being first is indeed a massive advantage. This exception arises when you’re not only first, but able to expand fast and continue innovate. Early mp3 players didn’t do this — they didn’t get huge traction and weren’t creative in hardware or design, which meant Apple had the space to innovate in design while the market was still largely available.

So yes it can work, and a well-funded startup combined with a stellar team and bit of good fortune can occasionally pull it off. But most little companies aren’t in that position, and it’s often not the best risk/reward position anyway.

What this means is that being “first” isn’t an end in itself — it’s not an advantage, not a feature, not a benefit the customer can experience. It’s a means to one of those ends — it can be levered into market dominance or it can be a manacle that locks your company inside a box.

It’s OK to be proud of being “first” at something, and you should be. But like being “disruptive,” being “first” isn’t necessarily desirable.

In any event, it’s not a competitive advantage. It’s just history.

Source: A Smart Bear | 2011

On the mid-market briar patch

The startup graveyards are littered with companies who tried to target this seemingly alluring [mid] market segment — customers small enough to be intelligent and nimble, young enough to embrace new technology, yet big enough to spend real money to alleviate real pain. It sounds like it’s best of both worlds. But the reality is: It’s the worst of both worlds.

They’re not “small enough to be nimble,” because at fifty employees they’ve already established much of the lumbering process and bureaucracy of companies a hundred times their size. Shackled by budgets and internal politics, technology changes require expensive coordination and retraining, and fear of change trumps potential rewards of improvement.

All this makes for an arduous sales process just like with big companies. But although they have the process and controls of a large company, they don’t have the budgets to match; there’s no large reward for successfully navigating the painful, Herculean sales adventure. Worst of both worlds.

Why is it like this? Maybe they’re stingy because they’re still being run by a parsimonious small-business founder (like me!) who is still straightening used staples to save pennies.

Maybe it’s because with a few dozen people, the segmentation of teams, departments, roles, and behavior is inevitable.

Whether because of physical limitations of communication or human tendency towards tribal behavior, we fall into semi-autonomous isolation coupled with formal processes to ensure command-and-control, and a bureaucracy is born, self-generating and largely inescapable.

Whatever the reason, it’s a tar-pit.

Source: A Smart Bear | 2012

On how a popular startup prioritization framework really works (or fails)

You know the geology-in-a-jar lesson from Stephen Covey: Schedule big things first, otherwise you run out of time. If you schedule little things first, you run out of time for the big things. If you schedule the big things first, then you can fill in with smaller things.

A common mistake is to think this applies only to the size of the work. That is, ‘Rocks’ means ‘stuff that takes a few quarters,’ ‘Pebbles’ means ‘a few sprints,’ and ‘Sand’ means ‘less than a sprint.’

This misses the most important point of work-ordering: It’s about maximizing impact by not allowing the easy nor even the urgent things to crowd out the strategic things that take years to unfold but are more important than everything else combined. A thousand “quick wins” do not add up to creating durable advantages or fulfilling a long-term vision.

Another mistake is to think that the previous paragraph is the end of the story. ‘Schedule revenue-growth stuff, then maintenance updates, got it.’ No. Each type of work requires different prioritization frameworks, has different goals, and hide different traps that make you unwittingly ineffective.

If you pretend these differences don’t exist, your team will be working hard and delivering lots of code-commits—the appearance of ‘productivity’—but they’ll feel like they’re not making progress fast enough, competition will start catching up, and they’ll (correctly) complain that they can’t see how their work is connected to the strategy.

The good news is: It does not take additional time to do it right. This is an instance of ‘smarter, not harder.’ You just need the right frameworks.

Rocks maximize impact

A Rock must deliver dramatic, measurable impact, not merely ‘incremental improvement.’ It must be strategic , meaning that it must attack the most important challenges you face, materially advancing the company down its unique path for winning its corner of the market, leveraging existing advantages to reduce risk and to forge a path that others cannot easily follow, and build new durable advantages. This is where teams most often fall short: Not delivering enough impact to justify their investment of time.

Sand maximizes throughput

Because Pebbles are the Goldilocks of work-items, it’s instructive to leap over them and solve for the smallest items, establishing bookends around the middle-child.

Pebbles maximize ROI

Pebbles are not a ‘balance’ between Rocks and Sand; they are their own creatures. Their timeframe is definitionally constrained between that of Sand and Rocks; the more important difference is that while Rocks are strategic, with a view towards winning over the next few years, Pebbles are tactical wins that have an impact in the next few months, attacking the challenges you’re facing right now, or a great feature idea you can surprise customers with sooner than they expect.

Source: A Smart Bear | 2022