Operate with a Clear Sense of Mission: Interview with Serial Entrepreneur Evan Frank
I recently went one on one with serial entrepreneur Evan Frank. Evan co-founded onefinestay, which was bought by Accor Hotels for $200M, and was later hired as the first external CEO of Context Travel, a globally distributed travel experiences business. Most recently, he co-founded Fora, a platform focused on bringing the travel agency into the creator economy.
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? What experiences, failures, setbacks or challenges have been most instrumental to your growth?
Evan: My career started in corporate finance, and then venture capital. The joke in banking is everyone wants to move to the 'buyside' - because investors were having more fun. But once I became an investor, it was the same thing - all the VCs I know really just wanted to be entrepreneurs.
So I turned 30 and decided to try building a company. After a short stint selling underwear on Portobello Road in London in an early D2C startup, I was invited to be a cofounder of an alternative accommodation startup called onefinestay. I loved the work. So I've spent the last 10+ years building new disruptors in the travel and hospitality space.
Certainly I've had my setbacks. One of the stark realities of entrepreneurism is that it's hard - every time. Certain things get easier - I now know the 'VC' way of thinking, how to hire and manage people - but there's no easy path to bringing something truly new into the world.
Every step of my career journey has had lessons that led me to where I am today.
Investment banking taught me the basics of financial modeling, presenting yourself professionally in front of people as a 22 year old who are much more successful and higher status than you, and attention to detail. But it also taught me how soul sucking, well-compensated, but ultimately non-passion aligned work can be.
VC taught me how to structure deals, how to source deals and prospect - lessons that I still use for BD and hiring today, and some of the psychological aspects of running a business.
My Portobello Road underwear business didn't quite work out due to some painful lessons around cofounder dynamics and the subtleties of what the tech world calls 'access to capital.' As a result, I always start new projects with co-founders and think carefully about the capital structure and investment configuration of any new idea.
onefinestay was a dream come true - but it was a difficult journey. We were providing a standardized high-end hospitality service in ultimately non-standard accommodation - people's real homes. It was an idea whose time had come - the best bits of an Airbnb and a high-end hotel in a single product. Managing big distributed teams created a lifetime of lessons around people management and the nuances of product market fit and unit economics. The ultimate lesson was understanding your cost of capital and how that changes quite dramatically over time, which ultimately led to a sale that was probably a few years too premature.
Context Travel was a wonderful family owned and operated business when I took it over, just after a small private equity fund invested. The pandemic was a harrowing experience to say the least, necessitating a total restructuring that I led from my bedroom while my kids were being Zoom-schooled. But it also led to a great innovation in online learning that's a fundamental part of the Context experience today.
And Fora feels like a fresh challenge with lots of hard problems to solve. Travel agencies are a highly-fragmented, mom-and-pop industry largely due to margin structures and being left behind from the online revolution in travel. No one looks at Expedia or Booking.com and says 'that's not a good business;' however, recreating an OTA with human powered labor requires a lot of technological innovation, payments innovation, and brand & marketing innovation. We think we're onto something big - but it's going to take many years to achieve our vision.
Adam: How did you come up with your business ideas? What advice do you have for others on how to come up with great ideas?
Evan: Personally, I really try to be a first principles thinker and apply themes across industries. I read broadly and really amp this up during creation phases - including daily newspapers, etc. What's going on in the world and where might there be a gap in the universe?
Some of the key considerations when we started Fora:
Compass had just IPOed, and I read that there were 3M real estate license holders in the US, the majority of which were not full timers. Yet there were only 100,000 travel agents. Why is there such a disconnect - especially given how fun a career in travel could be, as I observed in my cofounder Henley?
A WSJ article from March 2021 talked about 1.5M women who left the workforce due to the pandemic. There's many incredibly smart people in my life alone that have the time and the interest in a side hustle - or more.
Much of education and training was forced to move online due to the pandemic. This created the first opportunity to train up a remote labor force at no real disadvantage to being based in an office. The creator economy and cohort based courses also really exploded due to being stuck at home with a computer.
And so on.
Adam: How did you know your business ideas were worth pursuing? What advice do you have on how to best test a business idea?
Evan: I believe in the power of a long memo - sort of a foundational business plan. This forces you to put your ideas down on paper and examine ideas from all angles. There's also nowhere to hide - pitch decks can often gloss over the really important details.
I then share these memos with people whom I trust for feedback - including people in the industry as well as investors.
For me, the ultimate test is this: can you find cofounder(s) who you consider to be an equal in terms of intellectual horsepower, with complimentary skills, who wants to commit themselves as wholly and fully as you have to the idea.
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?
Evan: I view building a business as a milestone based activity. Often, these milestones dovetail with investment round milestones, and are essentially validating various hypotheses relevant to the company stage.
So for example: to confirm that we at least had a somewhat interesting opportunity at Fora, we wanted to validate that:
There was a large number of people who were at least theoretically interested in becoming travel advisors, and that we could, without years of time and unlimited budgets, reach them.
We could work with a subset of these people and transform them from never-having-sold travel before to actively selling travel advisors.
Validation of both of these hypotheses corresponded to the raising of a seed investment.
We actually feel that we've validated both of these hypotheses, so are now onto the next step in our journey which we see as proving out more of the commercial business model and depth of opportunity.
Adam: What are your best sales and marketing tips?
Evan: Try to avoid paid marketing! In my experience, Google and Facebook are just too good to profitably build a business off the back of them. Plus, these channels are increasingly technical and sophisticated, which means that organizational sophistication is needed to manage them, which means that the fully loaded cost of running the channels is often a lot higher than most companies fully appreciate.
So, try to build a business that's based on owned channels, and if you want to use paid search to get started, go in with eyes wide open.
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?
Evan: I think the defining qualities of effective leadership are excellent communication and transparency.
To take leadership to the next level, my advice would be to spend a lot of time with your team. Communicate the vision and why it's important. Share what's appropriate to share about the strategic direction of the company. Understand your team's career goals and how the company can be a platform to achieve these.
Adam: What is your best advice on building, leading and managing teams?
Evan: Building: for me, this is about hiring the best and never settling. Good is the enemy of great from a hiring standpoint. It's always possible to fill gaps in work that just needs to get done with freelancers or agencies - when making a hiring decision, the goal should be that this is a long term two-way commitment, assuming everything goes as planned.
I think effective leadership is all about understanding your teams. Life is short. Why does someone spend their valuable time at your company, working with you, versus all of the other potential opportunities out there? How does your company, and the functional role within your company, translate to helping them meet their personal and professional goals? How does the mission and vision of the company translate in a very real sense to the work?
And from there, I think management is about setting up a communication cadence and making the most out of time together. What's the big idea at the company this quarter? What are the key areas of focus? And how does this get distilled and cascaded down to the team level?
Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?
Evan:
Operate with a clear sense of mission. Doing anything new is HARD. There are many cold nights. It's the mission that keeps us going.
Play the long game - most of us have heard about the myth of overnight success, yet somehow feel surprised when overnight success doesn't happen to us. Commit to a big idea that's important to you, realize that there are HUGE opportunity costs in giving up your optionality, and work at it for years.
Every interaction is an opportunity to reduce someone else's suffering.
Adam: What is the single best piece of advice you have ever received?
Evan: It's hard to choose, but I would say two concepts from two of my favorite business books:
Good is the enemy of great. This applies across so many aspects of life and work.
Begin with the end in mind. In other words: have a plan.
Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also 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. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, 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. 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.
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