Don't Stop: Interview with Jamie Karraker, Co-Founder and Co-CEO of Alto Pharmacy

I recently went one on one with Jamie Karraker, co-founder and co-CEO of Alto Pharmacy.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? 

Jamie: In early 2015, my co-founder Matt Gamache-Asselin and I began thinking about starting a company together. Matt and I were both software engineers and met while working at Parse, a Facebook-owned company in San Francisco. We knew we wanted to work directly with consumers, but weren’t sure where to build a solution. So we did some research and settled on the pharmacy industry as our target because it was the closest thing we could find to a consumer product in healthcare. Then, after raising a seed round, we made a bold move to accelerate our learning curve in the industry and bought a small pharmacy in San Francisco.

Adam: What experiences, failures, setbacks or challenges have been most instrumental to your growth? 

Jamie: Learning how to manage my psychology alongside the marathon that is building a startup, and in particular learning how to de-identify with my company. As a founder it is natural to put everything into my company, and identify myself with it - if it’s successful then I’m worthy, if it fails then I’m a failure. The challenge with this mentality is that when the startup faces an existential crisis - which every startup does - it can feel like a personal existential crisis, which is not only painful, but also makes it more difficult to navigate the crisis at work. I’ve learned over nearly a decade of running a startup that this mentality is unsustainable. It’s been a long and difficult lesson to learn, but I now realize that in order to build true long term value, I need to have a healthy balance between devotion and unattachment. I care about my company more than pretty much everything, but I also know that I am more than my company, and my company is more than me. 

Adam: How did you come up with your business idea? What advice do you have for others on how to come up with great ideas? 

Jamie: Having spent years in Silicon Valley, we were already jaded by the tech ecosystem and were ready for a change. In thinking about what we wanted to pursue next in our lives, we noticed that other companies were not working on society’s most meaningful problems; they were focused on catering to the 1%. In contrast, we wanted to use our time and skills to build something that makes a tangible, positive impact on the daily lives of all people, especially those ignored by the tech industry. And so, we found ourselves drawn to healthcare — a big, broken industry that affects most people negatively, especially the underprivileged.                                       

Adam: How did you know your business idea was worth pursuing? What advice do you have on how to best test a business idea?  

Jamie: We were obsessed with finding a problem that actually matters to people. We honestly didn’t pay much attention to the viability of the business, or have much of an idea of what our solution was going to be when we started. But it was so obvious to us that the pharmacy experience was broken for people, and it mattered to them. But we didn’t have any experience in pharmacy, or healthcare, and we had no idea how to solve this problem or if it was even solvable, nor did we yet have any passion for this problem. So we immersed ourselves in the problem by buying a mom-and-pop pharmacy and living and breathing pharmacy for a year. We got to know the industry, the problems with the system, and the pain points of all the stakeholders involved. And over time, the right solutions to these problems became more clear to us, and we became extremely passionate about solving them. I’d encourage prospective founders to focus less on finding a business idea or solution, and more on finding a problem that matters. And even if you are not yet passionate about that particular problem, find something that truly matters to people, because it’s easy to care about something that makes a meaningful impact in people’s lives.   

Adam: What are the key steps you have taken to grow your business? What advice do you have for others on how to take their businesses to the next level? 

Jamie: The hardest thing for most product-oriented startups is finding an effective distribution channel, especially in healthcare. We solved this in pharmacy by going upstream from the patient, who doesn’t actually make most healthcare decisions, to the person who really controls the flow of prescriptions - the doctors. We figured out their pain points, solved those, and found a channel that is effective and efficient. Founders should focus not just on building the best product, but also on figuring out how to distribute that product in a scalable way.                 

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level? 

Jamie: Grit, candor, empathy. The most important quality in a startup leader is grit, persistence, and not giving up. It seems simple, but the only thing you have to do to have a successful startup is not stop. Candor is an increasingly important quality as the team size grows, and clear, direct communication is the lifeblood of an effective team. Empathy is the foundation of building a team that cares about each other, which may or may not be required to be successful, but tends to be more fulfilling.                        

Adam: What is your best advice on building, leading and managing teams? 

Jamie: Lead with empathy: Strive deeply to understand the thoughts and feelings of your teammates and people you manage, and prioritize their wellbeing.

Focus on impact: We prioritize impact over activity and focus on the work that makes the biggest strides toward our goals.

Be humble: Our work - however expert, technical, or specialized - is in service of our team, the people who use Alto, and the greater good. Everyone’s contributions count, and no one is too important to take out the trash, so to speak. And we are certainly not above other players in the industry whose mission to help patients aligns with our own.

Adam: What is the single best piece of advice you have ever received?

Jamie: Best: The one and only thing you need to do to be successful as a startup - don’t stop. Startups are a marathon, not a sprint - get your mind/body/life right, but be ready to drop everything and sprint on occasion. Build a team of people that you want to be in the trenches with, because it’s not just about winning but also enjoying the journey.


Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally-recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.

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Adam Mendler