Serial founder who bootstrapped WP Engine and Smart Bear into companies worth hundreds of millions; writes the blog A Smart Bear.
Jason Cohen's bootstrapped company SmartBear sold in 2020 for $2 billion with only hundreds of employees and a 50% bottom-line profit margin.
“it was sold in 2020 for $2 billion and it doesn't have 1,000 employees. It's super profitable. Like, uh, it was publicly said then, um, what the profits were. It's 50% bottom line profit.”
Cohen argues most pitches fail not because the idea is weak but because it's presented poorly. The same idea, re-explained well, suddenly lands as compelling.
“I mean, how many times has someone proposed something? Everyone's like, eh, I don't get it. But then someone else is like, look, what this is really about is blah, blah, blah. Everyone's like, oh, that sounds great. That I want. What you just said, you know, like what? I mean, that's just bad presentation. It's not bad information. It's bad presentation.”
Cohen's pet peeve: a slide titled 'Our Team' wastes the title since the audience can see it's the team. The title should state what's special, e.g. 'Our team has had 3 successful exits.'
“It should be the message you want them to take from that one slide. That should be the title. So it shouldn't say our team. I can see it's our team 'cause there's 3 heads and there's stuff. Let's just say something like, you know, our team has had 3 successful exits”
Steal thisReplace label titles ('Our Team') with the claim you want investors to remember ('Three exits between us').
Cohen searches a Twitter list filtered to people who posted in the last ~20 minutes and replies fast. Early, high-quality replies on big accounts get surfaced near the top and drive follow bumps with minimal time spent.
“I do a search where it's the first people on that list and they've posted in the last 20 minutes, which is a pretty small window. And there might be a couple other things like they have some favorites or I don't know if some, whatever. Okay. And I'll look at that and sometimes there's nothing in it. Sometimes it's just one or two, but I'll try to, if it's relevant to me, then I'll respond somehow. And because it was ju— it just got posted, it's much more likely that they will respond or see it.”
Steal thisFilter a list to people who posted in the last 20 minutes and leave thoughtful early replies to ride their reach.
Cohen argues a statistician would call both boxes equal at $10M expected value, but that misses the point: with one shot and unknown real-world probabilities, it's uncertainty, not measurable risk, so the sure thing usually wins.
“what you would say is there's no difference between the two boxes because the expected value of both box is $10 million. So they're the same. And my point is, no, they're not. Expected value is not the right way to evaluate the situation.”
Cohen argues a statistician would call both boxes equal at $10M expected value, but that misses the point: with one shot and unknown real-world probabilities, it's uncertainty, not measurable risk, so the sure thing usually wins.
“what you would say is there's no difference between the two boxes because the expected value of both box is $10 million. So they're the same. And my point is, no, they're not. Expected value is not the right way to evaluate the situation.”
Cohen estimates a genuinely rich American lifestyle now requires around $20 million, since 4% drawn annually is just under a million after tax once you account for inflation, taxes, and a balanced portfolio.
“probably more like $20 million, because you have to, you have to, there's a lot of things to do, but you have to think about averages and having a portfolio that's balanced and then taxes and then inflation. And so even 4% of interest taking out per year is actually kind of a lot. Given that you want to maintain it and keep up with inflation, et cetera. And that's where the $20 million sometimes comes from is, you know, 4% of that is like a little under a million after tax.”
Cohen's tell that public personas are fake: when a company suddenly goes bankrupt, its blog and last podcast the week before were always pure optimism — growing, hiring, getting profitable — proving the rosy narrative is bullshit.
“whenever you see a company kind of like immediately go outta business, go look at what they posted on their blog the previous week and go look at the last podcast they did. I promise you it was 100% optimism. Everything's going well. We're growing like crazy. We're getting profitable. We're hiring. People are loving. I guarantee it's all that the week before they went bankrupt. That just proves that it's bullshit.”
The same product can be framed as saving cost or generating value. Customers pay ~25% of savings to halve costs but will pay 100% more to double leads — order-of-magnitude more — because they already value leads.
“how much will they pay for halving the cost? I will pay some percentage of the cost that I saved. 25%. That's actually kind of high. Usually people won't pay quite that much. They should, they should pay up to 80%, you know, because why not? But that's not really how people think about it. So you could, you could maybe charge 25% of the cost you save. But if you say double the leads, what will they pay? What were they paying now for leads? A lot. What will they pay to double the leads? The same amount. They'll pay 100% more to double the leads”
Steal thisReframe your product as generating value ('double your X') rather than saving cost ('halve your Y') to capture an order of magnitude more price.
Cohen's company-building philosophy: optionality is power. Build a growing, profitable company with happy retained employees and customers so you can sell, raise, or go public on good terms but are never forced to.
“the way I think you should build a good company is you want optionality, the ability to sell and at good terms, but not have to. The ability to raise more money at good terms, but not have to. Right? The ability to go public, but not have to. Like optionality is power.”
Steal thisBuild a profitable, growing, low-churn company so every exit path stays open and none is forced.
Cohen says the firm's culture matters but the number one factor in a fundraise is which specific partner you get on your board, since the same firm produces wildly different experiences depending on the person.
“a lot of times people are like, should I, should I raise money from X where X is some venture firm? And the answer's always, Who at X? Because the firm is, is, there is something, because there's a culture and there's an attitude. It's not nothing. It's not nothing. But the number one thing is who at the firm. That's what makes all the difference.”
Steal thisWhen evaluating an investor, diligence the specific partner who'll sit on your board, not just the firm's brand.