This past summer I was invited to speak to a cohort of founders in The Hatchery’s Summer Accelerator. In all honesty, there are times when I’m in front of an audience like that where I feel a bit of imposter syndrome. While I’ve been an entrepreneur for going on ten years and have worked in technology much longer, I haven’t (yet) sold a company, nor have I sought any funding for one directly. In a world where talk of valuations, investment rounds and exits can dominate, sometimes that feels like a vulnerability.

But in front of this group I realized a more pragmatic value that I’ve probably underplayed myself, and that’s having clarity around what you are building toward, who you want to build it with, and whether those things are congruent with other aspects of your life. For me, I didn’t become a full-time entrepreneur until I’d already had a twenty-year corporate career, a couple of kids, and more than my share of bumps and bruises in a life that for better or worse has never revolved around things like cash burn rates and cap tables.

On that warm day in Atlanta I found a group of newly-minted entrepreneurs in development who posed questions to me that had little to do with how many stakeholder interviews they should conduct that month, or whether they yet had a proven product-market fit. Instead they wanted to know more about the personal side of entrepreneurship, which often doesn’t show itself in incubator applications. Their curiosity allowed me to reflect on my own approach and style to advising, which crystallized the questions I often ask to get at the person before we get into the venture. With that in mind, here are three simple areas where I like to start when I begin advising a new founder.

What does success really look like?

No one knows exactly where their entrepreneurial journey may lead, which for the most adventurous is a feature, not a bug. But somewhere between “build a unicorn” and “create a reliable side hustle” is a vast range of outcomes that can be considered more than acceptable. I was advising a student founder last year who had created a non-profit in the mental health space focused on advanced directives. She clearly had a passion for the work, which largely suffers from a lack of education and awareness. But she also wanted to go to law school, and didn’t necessarily like the idea of fundraising or chasing well-heeled donors, all but required to build a large enough non-profit organization from which to make a living. Ultimately she conceded that success could be a small non-profit running alongside her other pursuits, which in the future would likely involve being a lawyer. Something between a volunteer endeavor for a cause she clearly believed in, and a thought leadership channel to connect with people who might someday hire her for legal work.

The health and wellness space is growing exponentially, particularly in the areas of technology and AI which hold a great deal of promise to change both health outcomes, as well as our health systems as they exist today. Putting that environment of hype and potential riches aside is the reality that many people choose to be involved in health and wellness to make people’s lives better, not for how many zeroes they can add to their bank account.

Why is this important to you?

One of the things I enjoy most about the health and wellness field is so many people have a very specific “why.” A parent who suffered at the end of their life for reasons that could have been avoidable. Experiencing challenges through a child’s diagnosis or illness. Seeing the same health mistakes being repeated over and over involving people close to them. I have my own why, which admittedly came after I’d already been working in healthcare, but nonetheless has helped shape how I want to impact it going forward. There are many reasons why healthcare and overall wellness may be important to someone, and they often are way more personal than those in other industries.

As someone who came from the world of retail e-commerce and manufacturing earlier in their career, I explain all the time it just hits different when your work ultimately helps people, versus getting someone to buy something they may not otherwise need. For me it’s not about whether a founder has a good story for the pitch deck, but when things get tough, having that underlying passion may determine whether they survive the parts of building a company that have nothing to do with the value of an idea. A founder whose "why" is personal and specific might make different decisions under pressure than one who simply got into the space because the market looked attractive. It certainly doesn't predict success on its own, but it tells me a lot about how someone will behave when the plan stops working. And at some point, it will almost definitely stop working, at least for a little while.

If you’re looking for a co-founder, are your goals aligned?

The summer accelerator group had a lot of questions for me around how to choose the right co-founder or founders, and what criteria to apply. In most cases I turned the question back to them. Why do you feel you need a co-founder? What do you think you’re missing that you can’t just hire for? What would you have accomplished that’s different if you had one already? But I also explained to them that choosing a co-founder(s) is a lot like choosing a partner in marriage, with the main difference being that most likely you won’t stay business partners for a lifetime (whereas most hopefully do when choosing their life partner).

I also argued that you have to make sure you’re aligned on compatibility, which to me is even more important than the balance of skills and knowledge. In a healthcare environment it’s not uncommon to see a business person partner with a scientist, the classic Chief Executive Officer/Chief Science Officer pairing. Or a technical expert with a non-technical one. Those make logical sense from a business standpoint, but what they don’t guarantee is compatibility across goals beyond the business. Do you have similar expectations for where the business could go? If one of you is trying to build the next healthcare unicorn and the other just wants to control their own 9-to-5, that’s probably not going to work. Are you at a similar stage in life? While not a deal breaker, having two or more people in the same life stage is preferable to a mismatch. A younger, single co-founder may not appreciate an older one taking time away from the business to spend with their kids, for example. Being in the same or similar stage of life also makes you more likely to be aligned on expectations, as well.

There is no magic bullet or formula for determining the right combination of technical and soft skills to be a successful entrepreneur. But the right balance of clear expectations, authentic passions, and consensus amongst founders can absolutely elevate your chances above the rest.

Truth be told I didn’t really choose to be a part of the health and wellness sector of our economy, but in many respects, health and wellness chose me. First, upon co-founding Traktion Partners after a twenty-year corporate career in retail e-commerce, many of the early opportunities that came our way were in the health sector, which only accelerated after the pandemic in 2020. Second, a health scare in 2021 changed many things about how I managed my own personal health, from exercise and diet to mindful drinking, and everything in between. Third, I turned fifty and was forced to confront the realities of aging, including the fact that there are more Americans reaching their sixties at the same time than ever before (estimates suggest a staggering 1 in 5 will be at least 65 by 2030). How we prepare for that reality today will determine how comfortable getting older will be for all of us tomorrow. It’s no longer a hypothetical.

But my interest in health isn’t just a personal preoccupation, nor should it be. The societal challenges we face around health and wellness are too significant: a workforce staying active well into its sixties and seventies, a healthcare system still predominantly built to treat sickness rather than sustain wellbeing, and a generation of caregivers stretched between aging parents and raising their own kids (felt most acutely by my fellow Gen Xers now), often at the same time.

Shortly after the pandemic ended I began mentoring students at The Hatchery, Emory Center For Innovation, the entrepreneurship hub for the Atlanta-based university that’s located just a few miles from where I live in Decatur. At first I would take part in “Lunch and Learn” events, sharing lessons from our work at Traktion. Those talks led to being asked to lead Skills Builder Workshops with larger groups, eventually serving as an Innovator-In-Residence for the University’s Accelerator program. Those experiences taught me that I love being close to innovation, and if the students I’ve been able to meet are any indication, the future of work and innovation is in great hands. The founders and innovators working in this space aren’t chasing trends, but are building the infrastructure for how we’ll live longer, healthier, and more capably than the generations before us. This impacts how we eat and move, how we access proper care, and how we manage the little stuff long before it becomes the urgent stuff. That’s not a problem that is specific to any one generation, but touches everyone, whether they realize it or not.

I have reached a point in my professional life where I am focused not only on what I still hope to accomplish, but also on where to find fulfillment in my next phase. Transition can be a little bit unsettling at times in the messy middle, with one foot on the gas pedal, and a side eye on the exit door that suddenly doesn’t feel as far away as it once did. In that sense, finding purpose in the rapidly-transforming health space feels like the perfect spot to double down on each of those goals.