As a part of our series called ‘Five Things I Wish Someone Told Me Before I Became A CEO’ we had the pleasure of interviewing Luke Cooper.
KSerial entrepreneur, growth leader, and merger lawyer, Luke Cooper is Partner at San Francisco-based Preface Ventures, Founder and CEO of Latimer, and an Entrepreneur-in-Residence at Georgetown’s McDonough School of Business. In 2021, Luke founded Latimer with the aim to elevate the experience of Black tech entrepreneurs, provide training curriculum and advisory services to BIPOC founders, and facilitate strategic connections between investors, Fortune 1000 acquirers, and high growth companies. Luke sold his previous venture, Fixt,to Assurantfor more than 11x revenue.
Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
I started my career as an M&A lawyer in Baltimore, but after a couple of years and a couple of petty bosses, I knew that the only path for me was tech entrepreneurship. I didn’t want to waste my time worrying about whether I was wearing the right tie or carefully placed the quotations outside of the punctuation marks. So I scrappily put together a deal for my first company which was a $20M retail turnaround in Boston and failed horribly. My turnaround plan was predicated on acquisition of cheap debt to fix long standing problems but the world turned upside down in October of 2008, which happened to be 3 months after my acquisition. After staying home with my newborn son for nearly a year, in 2013 I revisited a problem I observed during my time as a lawyer for a Fortune 40 insurance company. I found that the claims process for smaller technology items like smartphones and watches was abysmal and that people often didn’t know how to submit a claim or even how to get them replaced on their own. Also, the price of smart devices was escalating while carrier subsidies were going away. I thought there had to be a better way to determine what broke and quickly align technical resources to repair or replace their devices easily. That led me to found Fixt and eventually pivoting the business toward enterprise where the problem expressed itself as $18B in corporate IT waste. I knew there had to be a way for employees to get their mission critical devices back up and running quickly. Turns out we were able to build an enterprise Saas platform that accomplished this inside of 4 hours for our F500 clients like AT&T, Honeywell, and Home Depot.
Can you share the most interesting story that happened to you since you began leading your company?
Before I sold the company, we were running out of money and I had to make something happen. I flew the cheapest flight I could find on Southwest, attended the Consumer Electronics Showcase in Las Vegas and stayed at the Strata Hotel for $60 a night, pretty much all we could afford. I didn’t even book the return flight. Instead, I hounded a friend to get me details and snuck into the Assurant VIP reception where I met the CEO and described to him the opportunity I saw to leverage Fixt to help them own the carrier and enterprise channels. Turns out we had a lot of shared consciousness around strategic direction and company building. The meeting was a smash and on the way out I bumped into a well-to-do colleague that flew me home on his private jet. Within 45 days of that trip the company was under Letter of Intent to be acquired and the rest is as they say history.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
From projecting $100M in Yr. 3 revenue to misquoting the size of the market by billions, I’ve made all the Founder gaffs you can think of. Like most Founders, we must exude confidence while very much leaning into the learnings garnered from customers. Coca-Cola was one of our earliest customers and when we signed with them, we had yet to perfect our algorithmic dispatch and service orchestration. The full platform just wasn’t ready however we knew we could just do it all manually. Well we never told the client that, believing they wouldn’t notice. When they figured it out, we got a stern tongue lashing but the service was so good that they wound up signing up as one of our earliest annual contracted clients. It forced us to commit to the enterprise path and build the right tooling specific to that market which ultimately led to 400% revenue growth and the eventual acquisition. Moral of the story, be transparent with early customers and let them lead you down the right path. Most entrepreneurs don’t realize that the game is played backwards and getting the customer committed to your mutual success will help you build the right thing for the right market.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
So many helped along the way. Eric Sauter, Charae Davis, Charles Hudson from Precursor Ventures, Larry Bernstein from EVP Investments and Joe Callanan from Blu Ventures come to mind immediately. They never shifted their supportive posture even when the chips were way down. Eric and Charae were a few of the many employees that were with me all the way to the end. They would seemingly do superhuman things to help us retain and grow our customer base. Charles flew in from SF for every single board meeting and Joe and Larry cut checks when at times when the struggle was real.
As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?
What less modern companies are missing is that DEI done right is their biggest hidden superpower. Black and other underrepresented people see around corners because they’ve had to for their whole lives. From talent acquisition to sales and product development, this can be turned on as a particularly significant driver of growth for modern corporate America.
The protests that we saw happen here in Baltimore and beyond are precisely about this issue and whether paternalistic dominance of women, or police abuse and economic disempowerment of Black people, I…THEY… WE are all saying that this has to change. I think I read an article by Ursula Burns recently that highlighted the fact that across 843 VC backed companies that have gone public, only 49 of their 4,700 board members have been Black.
As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.
I preach to my founders to get started on building culture and aligning around the vision as early as possible. It takes a lot more than just writing phrases like “we want diversity first” or “we believe in honesty” to define your core values. Those things should be expected in modern companies. I like to challenge leadership on why they select the values they do, whether they encourage or discourage deeper reliance on each other’s work, and how to make them actionable over time.
Here are two additional practical steps… stop reviewing LinkedIn profiles before the interview + take the authority bias out of the candidate review process. At Fixt, we only had 4 choices for selection of a candidate, (hard yes, hard no, soft yes, soft no) and we would all simultaneously write down and share our choices. We did this so the Founder or some other senior leader’s voice didn’t sway the decision. The end result was that 50% of our team was Black/LatinX and 50% of our senior leadership was Black. This doesn’t mean that a modern company only hires one ethnic group. More importantly it signals to the team that we won’t let bias alter outcomes and that we are truly returning to a place where our survival is dictated by our acquisition of the best people which often get overlooked due to small unconscious human biases.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?
I have a lot of shorthand for this question and some of my response depends on the stage of the company. I’ve seen companies at all stages from pre-Series A to pre-IPO to post F500 acquisition.
CEO’s have to be modern, that means they’ve got to master the big while minding the small, all while not letting process supersede equal and inclusive treatment of all. Not only does the job of a CEO differ in it’s reporting requirements to the board, it differs in a lot of what your day to day focus should be. Depending on stage and resources, the job requires an acute focus on broader strategic goals and the vision of the company. In today’s world whether partners or platform-based customers, the ability to sell from the CEO seat is also not undervalued. However, understanding how certain strategic sales have broader implications on your inorganic growth strategies and how best to position your thesis to the board, entirely the domain of the CEO and his trusted allies. These are skills that can be taught to anyone.
What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?
It’s” lonely at the top” is not exactly a myth but I urge Founder CEO’s not to accept this oft-quipped statement as fact. Yes. No one will fully understand you but work hard to build trusted relationships with people who aren’t afraid to give you an honest assessment of yourself.
What is the most striking difference between your actual job and how you thought the job would be?
The people element always amazed me. The stress of an early stage company affects each employee differently. I thought the folks that worked for me in my earliest days of building my last company were robots. Boy was I wrong. They grabbed me by the ear and taught me about the importance of constant breaks… they taught me how to use meditation and retrospectives to build new relationships to old problems… how to articulate complex business problems in concise standups that led to higher levels of execution than any of our better-funded peers. The people are always different than you think. Being open-minded is the key.
Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?
I think the skills I’m talking about can be taught to anyone because the most important trait is not intelligence. Lots of executives are smart but the exceptional ones are not just smart, they are also empathetic, great listeners, vulnerable (e.g., comfortable translating their imperfection into relatable lessons), data-driven (rely on data from a variety of disclosed sources to inform decision making), givers (work their hardest to understand the potential and ambitions of each team member and offers guidance to their goals).
What advice would you give to other business leaders to help create a fantastic work culture? Can you share a story or an example?
Define your vision, mission and values before you do anything else. In my experience this is the most important thing any leader can do. You get the most out of teams by aligning on culture and getting out of the way. I didn’t always do that well and at times it cost me great employees or even a customer or two. When we got it right though, we were firing on all pistons and operated with autonomy and precision. Employees want to own the work they do an when they own it they perform better. Our job as leaders is to give them a strong reason (vision) why they should commit their time and attention to it (the mission) and once you agree on the leadership principles (values), the values themselves become a crucial stakeholder in the path toward success.
How have you used your success to make the world a better place?
I invest my time and learnings into Black and other underrepresented groups every day. Any given day I’m fielding 10–20 text messages from Black founders.
Fantastic. Here is the primary question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
- Get a dog, get a therapist, invest in Crypto.
- They love when they love you, they hate you when they hate you. Don’t try to please everyone.
- Lean in deeply to feedback from the people that work around you even when it’s not favorable. It’s ok to look for patterns here.
- It’s ok to show up as your whole self… everyday.
- Victory is really evasive but really sweet too.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
I think all movements start with simple acts. If we want more fair and equal treatment of Black people in this country, an easy way to start is to simply speak to people that don’t look like you. Take an interest in their story. After all, it’s an American story. I would also encourage every person to pick up 1 piece of litter per day as they walk. Our waterways would instantly be 20% less polluted.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
Be present, even when it’s painful. Going through the mud is hard and we’re often tempted to close our eyes, but seeing the mud of life and reflecting on it as you move past it helps us absorb all of the rich lessons afforded by the moment.
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.
Love this question. Many of the people I’d love to interact with are post mortem. For example, I would have loved to meet with British Photojournalist Tim Hetherington before he was killed in combat while trying to capture the hearts and souls of kid soldiers fighting a war they didn’t understand. As for the living, here are a few:
- Will Smith: whether Red Table Talks with his Jada who is from Baltimore or any of his other media, he brings his whole self to every project in a way that is difficult not only for most producers but also most humans!
- Obama: ultimate example of calm under pressure, not just the pressures of international conflict and politics but also the calm under the attacks he faced as a Black man; I would ask him how he maintained not only his composure but also his
- MoneyBag Yo: he’s a rapper that is part of Yo Gotti’s label and I see why. Just like Yo Gotti he is wise beyond his years and infuses his life experiences and heart into every bar. The struggle to stardom in the streets that he talks about is the same mud to magic in tech entrepreneurship and Black CEO’s need to see the connection.
- The real Ted Lasso. I think his comedic inexperience is super akin to the journey of a first time CEO’s.