Jason Cohen — Two Exits & Two Unicorns
Jason Cohen’s journey from bootstrapping to raising millions with WP Engine provides a fresh perspective on the funding debate.
He discovered the potential for growth after two years of bootstrapping and decided to raise money.
Understanding competitors is important for developing a unique business strategy.
Rather than demonizing them, it is crucial to analyze and learn from them.
Raising Money: A Decision Driven by Potential
Cohen’s decision to raise money was not a part of his initial plan.
It was driven by the realization of the market’s potential and a desire for a different journey as a founder.
So there’s a lot of nice things. One nice thing is you are constantly evaluating yourself… So that kind of meta conversation is good. And then having some feedback. Now, of course, you’re gonna get feedback from all over the place online. So who knows which of it is valid or not? – Jason Cohen
To me, what’s nice about it is being able to be a human being and a successful entrepreneur and a dynamic human being and not have to pretend that I’m just sort of like this one way, but to be able to say, yeah, I have flaws, and I can talk about them. – Jason Cohen
If you don’t [hire people better than you], then the company will never get better than you personally are at every function, which is a complete failure of leadership. – Jason Cohen
Selling your business is bad, or fundraising is bad… that’s just counterproductive and silly. – Jason Cohen
No Conflict Between Bootstrapping and Investment
Cohen believes that the identity of being a bootstrapper does not necessarily conflict with raising investment.
He sees both approaches as having upsides and downsides, and it’s important to consider the actual behaviors and actions of investors rather than making broad generalizations.
So why did you do it again? Because he still needed to? I mean, maybe that’s it? – Jason Cohen
Positive Impact of Investors on Founders
The alignment between founders and investors can vary, but there are investors, like Swift Capital, who can make a positive impact by allowing founders to exit or providing continuity to the company.
Avoid Emotional Assignments to Businesses
Assigning emotional qualities to businesses is not a smart choice.
Viewing yourself as superior or others as dumb or evil based on their approach can hinder objective analysis and prevent you from understanding their strengths and weaknesses.
Importance of Understanding Competitors
Understanding competitors is important for developing a unique business strategy.
Rather than demonizing them, it is crucial to analyze and learn from them.
But yeah, it’s the nature nurture thing that bothers a lot. That bothers me a lot. Like not knowing if the thing that I’m doing is because I meant to… or if it’s something that I think I should do. – Unknown
Journey from Bootstrapping to Fundraising
Jason Cohen’s journey from bootstrapping to raising millions with WP Engine provides a fresh perspective on the funding debate.
He discovered the potential for growth after two years of bootstrapping and decided to raise money.
As a founder, who thinks you know everything, how fun is it? When other people have an idea? And you’re like, oh, okay, that design is amazing. That feature was incredible. – Jason Cohen
Being a relatable human being makes you immune to the allure of being a persona. Just being upfront about it, just saying it diffuses so much. It’s very, very different. – Jason Cohen
Hire People Better Than You
The misconception that founders should be able to do every job in their company leads to burnout.
It’s important to hire people who are better than you at specific tasks to create a stronger and better organization.
Learn from Competitors
Ignoring or dismissing the strategies and incentives of competitors can limit your own ability to develop a unique and effective strategy.
Understanding their goals and culture can inform your approach and help you carve out a distinct position in the market.
Thoughtful Evaluation in Hiring Process
Hiring someone better than you requires thoughtful evaluation during the interview process.
Ask questions about their approach to problems and evaluate if their thinking aligns with your own.
Building in public is you have to build a product and a strategy in which being a secret is not part of your strategy… It’s forcing you to make a strategy of growth, and even have competitive advantage that isn’t based around some sort of secret that probably other people can just rip off. – Arvid Kahl
And I needed to do something that gives back to the community that allowed me to do the first thing. So I started another business. – Jason Cohen
Focus on Fit and Environment in Reference Checks
Reference checks should focus on understanding if the candidate thrives in certain environments and if they would be a good fit for your company culture.
There’s bad actors in both places… I care about the actual behaviors going on rather than the concept of like fundraising being something that is or isn’t me. – Jason Cohen
To me, building in public sort of pushes or nudges you towards not having secrets, not trying to be something you’re not, and trying to win on your own actual merits and weaknesses…that is a better strategy. – Jason Cohen
Avoid Polarization in Business Stances
Stances on selling a business or fundraising should not be categorized as inherently good or bad.
Polarization within the community often stems from social media and the need to take extreme positions to garner attention and support.
Value of Nuanced Perspectives
Extreme simplicity in decision-making can be appealing because it reduces cognitive load.
However, it’s important to recognize that more complex and nuanced perspectives may lead to a more well-rounded understanding of a topic or industry.
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