7 aspiring founder personas

A framework for getting ready to start a company (including my own self-assessment)

Hi - I’m Mike Wilner, the writer of this post which is part of my weekly newsletter, Getting Shots Up. The newsletter includes frameworks, analyses, profiles, and musings about building entrepreneurial careers. This isn’t just startup advice – it’s a zoomed out view of how entrepreneurial people can think about constructing a career that results in a lot of high quality shots on goal.

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7 aspiring founder personas

“Should I start a startup or join one in a similar space?”

This is a good question that I get frequently. Entrepreneurial careers are long, and “just start a company” isn’t always good advice. You can also join other startups, work on side projects, help other startups on the side – all things that can accelerate your path to eventually starting a company some day and getting a high quality shot on goal.

There are three ingredients that I think founders need to align before I can confidently say it’s a great idea to start a company.

  1. Founder readiness: How ready and eager are you to start a company? Are you financially and mentally prepared for the founder journey?

  2. Opportunity: Do you have a clear vision for something that the world needs? Do you have a clear understanding of a market opportunity?

  3. Unique qualification: Do you have unique skills, domain expertise, networks, or insights that are different enough from others who would pursue similar opportunities?

Based on the combination of ingredients aspiring entrepreneurs have, they generally fit into one of 7 personas at different points in their careers. Self-awareness of where you are can illuminate the near-term career decisions that can put you in the right position to start a company – whether that be tomorrow, 3 months from now, a year from now, or 5 years from now.

Personas with one of three ingredients

If you only have one of three ingredients, then path to being ready to start a startup is likely a longer one. There’s too big of a chasm between where you are and starting a company to start a company today. Therefore, it’s worth taking a longer term view on how near term career decisions can get you to a point where you’d be ready to start a company.

If you have one ingredient, you should think about how you can acquire the other two ingredients. Usually you can work on both in parallel, but one may be more easily attainable in the short-term than the other.

Personas with two of three ingredients

If you have two of three ingredients, then taking the full-time plunge on your own startup would may appear logical, but would come with significant risk. You’re likely just one move away from having all three ingredients.

With two out of three ingredients, you’re on the cusp. If you want to start a company, you should consider moves that serve as a bridge to getting you your last ingredient before taking the plunge. Examples of near term actions that can help you acquire that final ingredient include:

  • High-risk founder seeking unique qualifications: Focus on building up the qualifications needed by talking to domain experts, becoming great at a requisite skill, or rounding out a founding team.

  • Ready-to-strike founder seeking an opportunity: talk to investors who might have insights on interesting market opportunities, chat with other founders who are working on interesting things, do customer research to try to uncover an opportunity.

  • Low-commitment founder seeking founder readiness: Go to therapy to make sure you’re mentally ready to start a company, make more money by doing consulting on the side to give yourself enough of a financial cushion to take the leap.


PETEY PAB' M –– *cough* excuse me...here’s my self-assessment.

I’m an excited contributor. I have an opportunity I know I want to tackle, but don’t have the unique qualifications or the founder-readiness yet. Here’s why.


I already know the opportunity that my next startup would address: entrepreneurial careers. I think the way that we think about careers and entrepreneurship is changing. Historically, “investing in entrepreneurs” has meant investing in their companies. In the future I think investing in entrepreneurs will evolve and include investing and supporting them over the course of 30+ year careers, even years before they start their first company. I think there are some really interesting opportunities to provide more life-long support to people who are building entrepreneurial careers.

Unique Qualifications

I’m also pretty qualified on this topic. I’ve started my own startup, mentored hundreds of founders, and have participated in (and supported) multiple fellowships that support entrepreneurial careers (Venture For America, On Deck). Through my writing of this newsletter, I’m continuing to refine my qualifications.

So why am I not uniquely qualified?

At this point, my insights in this opportunity space are not unique enough from those underpinning On Deck – “where top talent comes to accelerate their ideas and careers, surrounded by a world-class community.” If I were to start a company in this opportunity space today, it would likely be a poor competitor to On Deck, or On Deck would be better positioned to address any specific opportunity I go after in that space.

This is part of my motivation for (1) volunteering my time to On Deck so I can continue learning about what lifelong entrepreneurial support could look like, and (2) writing this newsletter. These contributions I’m making to the opportunity space are helping me develop the unique qualifications that I’d need before becoming an all-systems-go founder.

If I were to develop the unique qualifications before getting to a point of founder-readiness, then I’d become a low-commitment founder, I could start a more formal side project, try to incubate something related to this opportunity space within Amazon, and/or work on my founder readiness so that I could become an all-systems-go founder.

Founder readiness

Working at startups and building my own startup from age 22-28 was not good for my bank account or credit score. And now I’m 30 (gulp), so it’s becoming more important to create some financial stability for myself before taking another plunge. I’ve set some specific financial goals that I need to accomplish before I’ll allow myself to start another startup.

I’m also not mentally ready to found another startup yet. My first founder experience helped me uncover some things about myself and my work habits that I need to address before I’m confidently ready for the mental toll of being a founder again.

Addressing these founder-readiness gaps is a prerequisite to my starting another company in the future, and I’m working on them in parallel with trying to develop unique qualifications.

So, which persona are you? And what’s your path to becoming an all-systems-go founder?