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!


Note: This AMA is closed for new questions. You can check out the existing exchanges below.

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 crossing the predictability chasm

When you’re small there’s no need to predict when the feature will ship. Marketing isn’t scheduling a launch and recruiting isn’t timing the start-dates of the next 50 hires in customer service and sales. This means you can — and should! — optimize myopically for speed-to-market.

Small companies brag about their speed as an advantage, but it’s easy to see why the larger company actually has a massive advantage. Sure, when WP Engine launches a new product, the marketing department needs predictability for the launch date, but that’s because it’s a highly-skilled, well-funded group, which explodes with press, events, campaigns, social media, and newsletters, grabbing more attention in a single week than a smaller company might garner in a year…

The tradeoff, however, is predictability. We didn’t line up that press and have those sales materials and ensure code-quality high enough to scale on day one, without predictability. Predictability means going slower.

Predictability requires more estimation (takes time), coordination (takes time), planning (takes time), documentation (takes time), and adjusting the plan when it inevitably unfolds differently from the prediction (takes time).

Predictability is also required for healthy team-growth. Consider the timeline of adding a technical support team member. First, Recruiting is casting about for potential candidates. Then scheduling and performing interviews. Then waiting for them to quit their job and take a week off. Then new-employee-orientation. Then classroom training. Then paired up with senior folks on the floor as they ramp up their skills and comfort. Then finally, after (say) four months, they’re up to speed.

Since that takes four months, we have to be able to predict the demand for technical support at least four months in advance, because we have to be hiring for that future demand right now.

If we under-estimate, our support folks get overwhelmed with too much work, their quality of life suffers, and service to each customer suffers; if we over-estimate, we have too many people which is a cost penalty. Of course, the latter is a better failure mode than the former, but both are sub-optimal, and the solution is predictability.

‘The future is inherently unpredictable,’ insists the small company, spurred on by Lean and Agile mindsets. Indeed, blue-sky invention and execution are hard to predict. But this is also a self-fulfilling prophecy; to insist the future is unpredictable is to ignore the work that could make it more predictable, which of course makes it in fact unpredictable to that person.

Small companies don’t have the data, customers, institutional knowledge, expertise, and often the personal experience and skillset to predict the future, so they are usually correct in saying it’s impossible. But it’s not impossible in principle, it’s impossible for them.

At scale, it becomes required. Not because Wall Street demands it, or investors demand it, or any other throw-away derogatory excuse made by unpredictable organizations, but because it’s critical for healthy scaling.

Source: A Smart Bear | 2017

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


Really looking forward this session, Jason!

Thank you for taking the time!

— You’ve described Heather Brunner, WP Engine’s CEO, as “the founder who joined three years in.” You’ve also previously started companies both as a co-founder and a solo founder. What are some helpful considerations for someone pondering over the co-founder decision early on in their journey?

— Your post on the traps of low-knowledge, high-confidence theories is a timeless reminder. It’ll be instructive to hear about some of the day-to-day practices at WP Engine that have helped the team steer away from snap judgements and deliberate better.

— In terms of early-mid stage hiring, what were some truths that were hard to accept for you at first, but in hindsight have proven central to how you’ve scaled teams in recent years?


Thanks so much for doing this AMA, Jason!

Your long-running blog (A Smart Bear) belongs to a truly special category which includes another favourite of mine, Joel Spolsky’s Joel on Software blog. Founders who’ve documented what it really felt like to build a business in those uncertain early days of SaaS.

I really believe that these writings have collectively shaped the first building blocks of the industry (they’ve also inspired why and how we’re building Relay as well :)). So, thank you for continuing to reflect, observe, and bringing important things to light for fellow founders.

Had some loosely connected questions I’d love to hear your thoughts on:

— You had once written about how large, profitable companies with brand moats and reliable revenue streams present startups an opportunity for Innovator’s Dilemma-style disruption. Now that WP Engine is that huge, profitable business with market dominance, how do you think about disruption?
— On the question of building efficient businesses, in hindsight, how has your experience of bootstrapping ITWatchDogs and Smart Bear, made WP Engine’s VC-led path unique? Any specific decisions that you feel more VC-backed startups should pay attention to?
— Then, finally, what made you choose Silver Lake, a PE firm, over a late-stage VC?


Hi Jason - love to see you participating here (and have really enjoyed following you on Mastodon, too). My big picture interest is around how you’ve inspire and incentivize folks on your teams to do their best work.

I’ve noticed in my career that folks I work with will sometimes make extraordinary, high-quality contributions, and other times lackluster ones. It seems to be the case that people are capable of a massive range of accomplishment, which directly conflicts with the classic startup-founder view that there are “A” players, “B” players, and everyone else.

So, two specific Qs:

  1. Are you generally in the camp of “environment can massively change a person’s contributions to the org” or “you should hire ‘A players’ because no matter what the environment, those people will bring A quality work?”

  2. What’s been your experience with getting folks to contribute their best work, and what advice would you have for other entrepreneurs seeking to make the most of their teams?


Excited to see you doing an AMA here, Jason. Thank you for sharing your wisdom throughout the years.

Here’s the Q:

How do you find energy and motivation to keep teaching others — vs investing the same effort into growing your companies? At what point in your journey did that become a calling/priority?


Hey Jason, it’s great to see you here. As I’m building my second company, I’m curious about your experience, could you share any mistakes you made while building your second company that you managed to avoid in your first venture?


Happy to see you here, Jason! Your post on Rich vs. King was super helpful to me when I was selling my last company back in 2014. I’ve shared it with many founders since.

I’m curious how you’ve navigated the “Freedom Line” after crossing it the first time. In my own experience, it’s tempting to move the goalpost. I started another company in 2020 and raised a seed with the idea that that would be all the cash we’d take. Now it’s growing fast, profitable, and I often wonder if we should continue on the path we’re on building a solid business, OR raise more, raising our ambition and (potentially) our stress levels along with it.

How did having financial freedom from selling Smart Bear change your risk calculus when starting WP Engine? What did you learn along the way?

Bonus question, if you feel like it: Your company’s five people, growing like crazy and you’re all barely keeping up. What are the first three things you’re delegating off your plate?


Hi Jason! I’m a big fan of your writing and blog. Having built Smart Bear and now having scaled WP Engine to an organization of over 1,200 people, I’m curious how you think about management and leadership and if you have any simple wisdom to share about what’s worked for you. Have most senior managers been hired in from the outside or have they grown with the company? Are they any particularly painful mistakes you’ve made that we can learn from? :slight_smile: Thanks so much!


Hi Jason, thanks for participating in this AMA.
I would like to pick your brains on the topic of Customer Empathy
As companies scale, various teams, including sales, solution consultants, and customer support, among others, act as intermediaries between the product development teams and the customers. Unfortunately, one unintended consequence of this arrangement is that customers begin to be perceived as abstract entities by engineers (and to some extent, product managers as well). Consequently, maintaining customer empathy becomes increasingly challenging. Roadmaps, KPIs, and internal milestones often take priority over addressing customer pain.
I’m curious to know if you have any suggestions on how to ensure that the “customer first” culture remains strong in teams that do not directly interact with customers as the company continues to grow.


So so excited to see you doing an AMA here Jason. I have been a fan of A Smart Bear since I was practically a kid!

You’ve experienced what is, for many, the startup dream: to build a “unicorn” business. You’ve also built smaller, successful businesses, too.

Do you have your own definition of “success” and what it means to you? Is it to reach a certain milestone in terms of wealth, lifestyle, freedom, or other?

If you do, how has that evolved over the years as you have gained more first-hand experience and exposure to both smaller and larger businesses and the lifestyles that come with them.

Thank you in advance, and thank you for teaching me so much over the years.


Thank you for the great questions!

I believe there are people who thrive by having a shared experience, and people who thrive by being the top person. The older you get, the more experience you get, the more you know which you are. This is the first factor for deciding. The default should be to go with your personality.

Statistically, most companies that succeed have co-founders. That’s not the same thing, however, as saying that companies are more likely to succeed when there are co-founders. (It could simply be that most companies have co-founders.) Also co-founder strife is a main reason companies fail. So I think of having a co-founder as a high-beta choice — it might be more likely to help you succeed as well as more likely to be a source of problems. Generally speaking it’s not a bad idea to have high-beta things, since everything is unlikely to succeed, so getting any possible advantage is probably good, even if it comes with risk.

Generally the positive co-founder stories involve people who have worked together before. Otherwise it’s like getting married and moving in together and have a baby before dating. It could work, but probably won’t.

How to deliberate better
Just because you’re more humble about what you really know, doesn’t necessarily mean you should deliberate a lot. Deliberation is good when it will increase the quality of the decision, i.e. de-risk it, or improve the details. When gathering more input and more discussion results in something better, that’s great.

But often it doesn’t result in a better decision. Over and over, we’ve done customer discovery, learned what customers want, built something, and it isn’t what they wanted. Or we’ve analyzed some market segment or competition, and it turned out to work differently than we expected. It’s still true that we shouldn’t have high confidence in our theories, but deliberation didn’t help.

The world is more unpredictable than we think; here’s some specific strategies to deal with that: Navigating the unpredictability of everything

Also sometimes a decision should have more deliberation; here’s specific ways of knowing when: When should a decision be fast, or slow?

Hiring during scale
Specialists are important. Early on, they are not. You often cannot take advantage of them. (Sometimes you can, like in design.) But at scale, the details are important, the experience with everything that can go right and wrong is important, the pattern-matching is important, seeing the movie before so not everything is reactive is important.

It’s also a huge advantage, because it means your team is dramatically leveled-up. But a lot of it will feel wrong to your current team. The smart people who “just figure it out” might not understand the value of experience, or that we no longer have time to “just figure it out,” or that doing that affects dozens if not hundreds of people when you get it wrong. It’s a different kind of person — the kind who joins a scaling company but not an early startup, whereas the existing employees are definitionally the other way around.

It’s tough to navigate the “culture” that you have, when in fact things about people and processes and methods must change.


Disruption, once at scale
Yes Innovator-Dillema-style disruption is one kind — where tech starts out cheaper but worse but different, and then becomes better. There’s other kinds too, like right now where their world is disrupted by AI, or some businesses are disrupted by economic conditions (enough to bankrupt some companies and thus change market dynamics).

For us, a big potential disruption is the platform risk of WordPress itself. Still 43% of the Internet and still growing, but of course there are many SaaS alternatives (e.g. Wix, Squarespace, Webflow) and vertical alternatives (e.g. Shopify, Toast) as well as new architectures (e.g. headless). None of those are ID-style (e.g. no one thinks headless is “just a toy”), but they all encroach on the overall website market.

So that’s how we look at it — major trends that change the landscape of “having a website.” When we were smaller, these possibilities were true but irrelevant, because the WordPress market was (still is) so large, that for a small company these other trends don’t matter. But once at scale, market-level changes do matter.

Can VC-funded business learn from boostrappers?
Definitely, both can learn from both. In general, people can learn from people from other industries or timeframes.

That said, the goals are difference, and the resources available are different, therefore you have to be careful about what “advice” you bring over.

For example, boostrappers love to scoff at how VC-funded companies prioritize growth over profitability, saying that means they’re “not real companies.” For business models that can never be profitable (e.g. Uber, WeWork), I agree with that. But many of those companies were unit-profitable even early on, therefore it was obvious that the business model would be profitable once at scale, and therefore “grow fast” was in fact the correct goal, fundraising to spend sooner than you would otherwise. Many of the public SaaS companies are profitable, and most are cash-flow positive, proving the point.

So, saying “companies should be efficient” isn’t quite right. Bootstrappers must be efficient at everything, but at the expense of many things — not just growth, but security and finance and legal for example. Having seen and even purchased a number of bootstrapped companies, I assure you they do not pay taxes properly, often disregard the laws of many jurisdictions, and have major security flaws. Is that something VC-funded companies should copy, or should they use their extra funding to do better on those fronts?

I do think all companies should strive to be unit-profitable, i.e. “profitable once at scale.” There are various metrics you can use to determine this. GPM is fine for operational unit-profitability (BTW bootstrapped love to ignore support costs and market-rate salaries as they claim to be profitable and have high GPM), but ignores high-CAC which is often a real problem for VC-funded companies.

A metric I like is a made-up one called EBITDASM, which means EBITDA but also without Sales or Marketing. The idea is that “if we stopped spending money to grow, would we be profitable?” If no, you cannot claim “the only reason we’re not profitable is we’re growing so fast.” Even if yes, you still might have a CAC problem, but at least that’s tied to growth as opposed to having fundamentally unprofitable operations. So you could use EBITDASM to monitor at-scale profitability (and decide if and when you need to invest in increasing it), and something like payback period (or Magic Number, which is just the reciprocal of annual payback period) to measure GTM efficiency.

Why SilverLake?
SilverLake is an S-class firm — the very top. It’s hard to imagine a late-stage company, who wants to raise money from someone, who wouldn’t want to raise money from SilverLake.

I think the difference between PE and late-stage VC has shrunk in the past 10 years. PE and VC used to be very different; it’s still is at the very small end, but in the 100s of millions of $$ and higher range, I’m not sure that it’s different. In both cases it’s a lot of money, you’re driving governance and maturity as much as the product, and the potential outcome modes are the same — selling to another PE, going public, selling to a large, cash-rich, probably-public company.


I’ve noticed the same. I don’t thing that means there’s no difference in talent between people, however. I do agree that “just hire A players” is too simplistic.

Can the environment massively change a person’s contribution?
Yes, in either direction. A poisonous or process-mired environment can take the best person and render them inoperative if not worse. A great environment can bring out the best in people, and they can perform better than they themselves ever thought possible.

I don’t think that means there’s no difference in people. Rather, there’s innate attributes that intersect the environment. Think of the A player as a strong swimmer, who loves to swim. So when the water is high and rough (tough times), they can swim and survive, and perhaps they even love the challenge, because great people love to exercise their greatness, especially with others who can keep up. When the water is medium-height and calm, they can do whatever. If the water is low (too easy, no challenges), they’re bored. They’ll “survive,” but they want to do more than survive, they want to swim, so they go somewhere else.

Now there are people who can swim but not well. If the water is too high, they don’t make it. If the water is calm, they can survive. These might be B players.

At any given time, a company might have different water levels, even different team to team. It’s possible that one team is in a great, healthy place, with no need for urgency, even doing A+ work. There, a so-called B player might fit in well, and improve just by being surrounded by great people and great process, to learn from or just to not drown in. But another team might be in the chop, and you can’t put just anyone on that team for them to turn it around and not just survive but thrive.

I also believe that some attributes can be changed, and some not. How much of that is built in, and how much of that is will, and how much is whether the environment is supportive and conducive? I don’t know. But I know that when I run into someone 10 or 20 years later, some things are different and some are not.

I also believe in “fit.” That is, it’s possible that a person is a so-called B-player in one position (or company/culture) but an A-player in another. In fact, we all are. I can easily find situations where I’m an A++ and where I’m an F. So I wouldn’t label the human a letter grade overall, but I do think you can say where strengths and gaps are, or where fit would be great or not (even if not with a letter grade). In a sense, you could say this is environmental too, but not because the environment “changed the person” but rather that having “person / environment fit” allows the person’s strengths to shine.

How to get the best work out of people
You get what you expect, and you get what you model.

When your attitude is that the team isn’t working well, and lots of things need to change, that expectation is felt. When your attitude is that this team has all the ingredients of greatness already, and just needs a shift in policies or procedures or letting go of certain constraints or adding some enabling constraints or changing their philosophy or replacing just one “bad apple” person, or…. then that expectation is felt too.

Mostly though I find that modeling is the way. When I’m engaged all the time, asking questions, poking in Slack, discussing in documents, asking “why not faster” or “what’s another way,” then others do too. Maybe they want to impress me. Maybe they now see that something better is possible. Maybe they’re just inspired by the energy.

Another thing I think is very important to model is honesty, especially about whatever is “bad,” and with a constructive mindset. When I dive in with a team, I specifically look for things that’s “bad” or a “mistake” or “broken” or a “failure” or other words people like to use, and then I call them out, and then explain why this is not a failure at all, but rather this is healthy and the way forward.

Example: If a feature we released doesn’t have usage, I say how great it is that we measure usage, so we can know that and do something about it. I say that all teams make features and sometimes they’re not used — that’s life! We don’t love that obviously, we’d rather that didn’t happen. But there’s no such thing as a team that never makes a feature that isn’t perfect. We’re so good, however, that we’re able to detect that, and then do whatever we want. We might want to kill the feature, or iterate it, or ask more questions of customers, or whatever else. Team decides because the team is in command of the situation. That’s why it’s not a “failure.”

When you can be honest about “bad stuff,” and see that “being in command and trying to be smart and trying to do the right thing and being honest” is actually the expectation, then the team is free. Free to celebrate wins and call out misses and stay in command. That’s fun.

I believe this sort of thing brings the best work out of people.


For me the writing and teaching and doing things like this AMA is an extremely enjoyable hobby. It’s selfish really — it’s not for money, it’s for ego, a small amount of fame, for not only being able to work out what I think about things, but then have an endpoint for the final formulation of those thoughts (i.e. articles that people generally enjoy and sometimes really love).

Because it’s a hobby, and fun, it’s not a question of whether I write or put effort into the company. It’s like saying “why do you play chess or play the piano, when you could be spending that time working on the company?” Because sometimes you need to “rest,” for some definition of “rest.”

Most things I write come from things that happen at WP Engine, or when I’m talking to other founders. And the formulated ideas and frameworks that I write about, I can use at work. In that sense they are symbiotic, although that is not the explicit goal, and I don’t worry at all if that doesn’t happen.

I’ve always loved teaching, so it was always part of me. In college I tutored calculus, and I especially liked finding (what I thought were) much better ways of explaining concepts. So, like starting companies, it has just always been a part of my personality. I’m just lucky to be living in a location in the total timespan of humanity where I can write articles and others read it, from the comfort of home, and as a hobby.


I — just like you it appears! — was wary about making common second-time-around mistakes. As such, I think I avoided anything major. I cannot point to a moment at WP Engine, for example, where there was a large misstep that had to do with it being the second company.

A common mistake is thinking you can shortcut the product and market and customer learning. That just takes time. You can probably have better tools and processes for doing that work, which might accelerate the learning relative to not having those tools, but it still will take years, not months. I’m sure you know that already though!

The things you can truly short-cut are the things that definitionally haven’t changed, like how to do bookkeeping, or the main lines of the law, or the fact that you don’t need insurance at first. That’s helpful, but of course those help at the edges, rather than solving the most important problems of the early startup, i.e. initial product, initial distribution, initial competition, the reality versus what it appeared, figuring out why everyone is cancelling or no one is converting, plugging the egregious bugs in the software, and so on.

A huge thing I did right the second time around, that I did totally wrong the first time around, is the second time we had a real, intentional culture. The first time I thought that was touchy-feely stupid stuff. As a result, our culture was a mixture of things I liked and didn’t like, and I ultimately burned out. The second time around we had a great, intentional culture, and 13 years later we still do. And I moved from CEO to CTO and now to a special “Chief Innovation Officer” position, which prevented burnout while allowing me to contribute things the company needs, using my strengths. (Here’s exactly how I made that decision over and over, and you can too: Finding Fulfillment)

I think if you keep the notions in that article in mind, and also keep beginner’s mind — i.e. “I still have everything to learn, all over again,” then you’ll be in good shape. I think people mainly go wrong when they don’t have that beginner’s mind, so they think they know everything already, and don’t need to do the work. That’s true only with specific things that are the same for every business.


Thank you so much for those kind words!

Freedom line affecting the next company
Clearly the question of personal goals is…. personal! I’m happy to answer, but there’s no reason to think it applies to any other particular person.

I started WP Engine as another bootstrapped company, with bootstrapped goals — profitability and fun. It’s true that I had more runway to try things and fail, and surely that was an important factor in how I thought about risk. In particular, the second venture can be more risky than the first, because you now have the money to throw it away and do something else. But my nature is not risk-taking, so although I’m sure this was a subconscious factor, I built WP Engine only after a lot of customer interviews (and decided against other ideas before it, also because of customer interviews), and cautiously. Until, two years in, it was clear that the opportunity was much larger than I originally thought, I raised a small first round, growth kicked into hyper-growth, and the rest is history.

If I hadn’t seen that much larger opportunity, would I have switched from bootstrapping to fundraising? I’m not sure. I do remember thinking at the time that it would be fun to have a different sort of adventure this time around, i.e. where cash is available and the goal is high growth, as opposed to where cash is scarce and the goal is profitability. So I do think being on the other side of the freedom line changed what I was open to. But it was more like I was open to something new when the possibility arose, as opposed to starting the venture already thinking “this time, swing big, because another small win wouldn’t be interesting.” I never thought that way.

It would make sense for money to change how I evaluate what venture would be fulfilling or interesting or worthwhile or the “right level” of risk vs reward, but the fact is, it didn’t. I’m just who I am!

What to delegate at 5 people
This is impossible to answer in detail without context, because it depends on what the company needs, what you and your team is currently capable of, and what you and your team currently love. Also you said “we’re barely keeping up” but also “we’re profitable,” so I’m going to assume the question is “what do I delegate… which I will pay for” whether that’s another employee, a contractor, or some other service. (After all, if the entire team is underwater, then you can’t really delegate anything, because it means someone else is now completely trashed.)

But I can answer it broadly. First, I’ve published the framework that I use for myself. This details the Joy + Skill + Need that I mentioned above. I’ll let the article speak for itself on how to solve that equation.

Second, I once heard great advice on delegation: There are things you’re terrible at (A), things you’re just OK (B), things you’re excellent at (C) and things which are your superpower (D). It’s easy to delegate (A) and (B), because you know you’re no good anyway. Especially with (A), the struggle is that you don’t know how to hire and hold accountable the people who do that, because you yourself don’t know. The answer to that is: Too bad, as an exec-level leader, that is your job, and no one more than CEO. The CEO had better hire people who are much better than her at every position, otherwise the company isn’t getting better.

Now, the difference between (C) and (D), is that with (C) you are an expert, but you had to work very hard to become that. You might have went to school; you certainly have put in a lot of time. You have lots of opinions about it, and you’re genuinely great at it. But it’s exhausting. If you do it all day, you did a good job, but you’re wiped out. (This is the Skill - Joy trap in my article.) This is why you should delegate it, despite you being great at it. You do know how to manage, because you have opinions. But be careful to still allow them to fly — the trap is micromanaging them because you have valid opinions. You do have those, but you need to hire someone good enough that you’re not micro-managing, otherwise it’s not really delegation.

What (D) looks like, is that you barely even know how good you are. It’s just what you do. Others are amazed, but for you it’s just life, and in fact you probably are disappointed in your own performance, but really it’s because it comes so naturally, and your standards for yourself are so high. (In the negative case, this becomes Impostor Syndrome.) When you do the thing all day, you are energized and still want to do more. These are the things where you achieve flow state. Or when you do it for hours and just feel so refreshed and good instead of tired, like an extrovert after a party.

You shouldn’t delegate (D) things. In fact, the ideal is for everyone in the company to be in (D). When you read that article, you will see these ideas in there as well.

Of course, all of this is an ideal only — my article and the A, B, C, D. Life is never so clear or possible to arrange. However, it is a direct answer to your question: Seek this ideal. Wherever you can advance towards the ideal, do that.

First you have to ID the ideal for each person, but this can be a wonderful exercise. You might already be able to shuffle some things around to get closer to ideals. Also, seeing these things laid out, might help brainstorm “what could I do to address this.”


Thoughts on management and leadership

I’m not sure I have unique things to add in the very well-worn subject of management. Specifically to your question, we’ve had both success and failures in internal hires and external hires, so all four squares of that virtual 2x2 have a lot of examples. It just shows that there aren’t simple answers to those questions.

One thing that I don’t think is mentioned often, is that the pace of growth of the company matters a lot. In a self-funded company that grows slowly (if profitably) over time, like Smart Bear, people can grow as fast as the company needs that growth, so it’s easier to hire “from within” into management positions. (Although it still helps if several people at the company already have that experience, so everyone isn’t making the rookie mistakes simultaneously, with no support or advice.)

On the other hand, if the company is scaling rapidly, most people cannot grow fast enough to match, especially since the problem change quickly, and not having solved them before becomes a serious liability. “We’ll just figure it out as it comes” works very well at small scale and when things aren’t changing fast; it’s a terrible process when things are scaling and there’s no time to “figure it out.”

Another bit of wisdom that I gained at WP Engine through other great leaders, and which can be applied to the above problem as well, is the following:

A team can be very effective and high morale if one person on the team is struggling, but not more than one. So for example if you’re a VP of Sales, and you have 4 Directors who are doing great and 1 that’s not, that’s still a healthy team. Peers can help, and the leader has time to help, because only one person needs a lot of attention. There’s a lot of positive examples to draw from, since peers are doing well. If this person has the potential to be great, then it’s a good use of time to work with them to get them there. If that eventually proves impossible, then you do need to replace them, but still be proud of first trying to help.

This is generally useful, and specifically can be applied to the question of “hiring inside vs outside.” Often an inside hire means having the advantages of their institutional knowledge, zero culture risk, and excitement at being given the chance, and the disadvantage of not being able to do the job well on day one. So, if the team is otherwise healthy, this is a perfectly great situation. But if the team is already struggling, adding another person who is struggling, is a bad idea.


How to generate Customer Empathy from engineers and others far from the customer

This a great observation and a good question.

I think the main way to generate empathy is direct contact. You don’t need heavy processes or rules, you just need direct contact. Go on sales calls and just listen and ask questions. Go on support calls and just see. Sit with support and work tickets. Go to a trade show and work the booth. Do an online event and participate in the chat.

We used to rotate all engineers through support a few times per year. “In support” means anything – just sitting with the team, laughing about stuff, looking at chats and tickets. If they can help solve something, even better, but that’s not a requirement. Just experiencing it is the only requirement.

Everyone always comes back from a week of that with a renewed sense of the customer, and a head buzzing with ideas of what we should do. Especially when some of those things are simple.

So, no one has to become a designer or product manager, or an expert on prioritization or even problem-solving. Just be there periodically.


Thank you so much, and I’m happy to have been part of your formative experience. :slight_smile:

What is your definition of success?
Well you’re surely already familiar with how I thought about that in 2007 when I sold Smart Bear, so that’s one way. But now, with WP Engine an even larger success financially and personally, it does beg the question again.

When I made the decision to become the CTO rather than CEO of WP Engine, I had developed a simple system that originally was meant to avoid burn-out, but also somewhat answers this questions of success. If I’m doing something I really enjoy doing, that exercises my strengths, and it is needed by others, that’s fulfilling, and thus a day-to-day answer to the question.

On a longer time horizon, I think I haven’t figured it out yet, other than the obvious things like enjoying the work, finding meaning in it, minimizing the things that are both (a) unpleasant and (b) unimportant but necessary.

Maybe it isn’t more complicated than that. I think the challenge might be in answering: OK, but what do I personally find enjoyable and meaningful? And less about what the overall framework is. Sort of like how you don’t really need more frameworks and research to know that you should eat well and get some exercise, so the question is what diet works for you personally, that is effective and not so unappealing that you can stick with it.