Over the course of 4-5 years with a start-up, I got a first-row seat into the ups and downs of scaling a company. One of my main takeaways was that you have to enjoy the journey. If you only seek the destination you won’t last the trip.
And to enjoy the trip you have to work with people who make the miles a bit more enjoyable. You don’t have to like them and hang out on the weekends, but you have to respect them. Respect their perspective, their experience, and their contribution. Respect enables trust and trust is a prerequisite for a healthy and long-standing relationship.
During my tenure I worked with some world-class professionals. In some cases our trust was more or less immediate (out of necessity!) and in others, it took a few crucible events to crystallize our bond. While there are too many names to write down, I do want to acknowledge the significant positive impact a few individuals had on me during the process:
Kevin Stevens & Jonathan Crowder: My “go-to” team from Dallas. No job was too complex or big for these men. They taught themselves operational finance, product management and the essential of programming. Whenever we were busy I knew they could pick up the slack. And when times were tough, they knew how to strategically engage and re-position the argument to identify channels for growth. Big things ahead for them as they take on the Texas market.
Kerry Cooper: Kerry brought institutional leadership when we needed it most. She brought excellence in hiring, in thinking about the customer, and in establishing operational procedures & OKRs. At the respective moments, most of those traditional managerial were relatively new to me. In addition to management lessons, I also learned from Kerry how to engage a mentor network, voice my opinion more effectively and to be willing to have an open and honest debate and feedback. I was lucky that her experience from Levi’s, Walmart, and ModCloth brought valuable lessons to my career.
Jay Webster: Early on Jay gave me the flexibility to explore growth, taught me how to simplify strategy and most importantly how to execute. Within my first few weeks I was stunned at how much accomplished rolling out to new markets and testing new partnerships. I also appreciate his lessons from many start-ups on how to better pitch VCs and how to engage a board room. Finally, I still marvel at how he could perfectly match interpersonal strength with candid feedback – truly an exceptional leader.
Ethan Wais: My first hire who was always the smartest guy in the room. He saw the future faster than most and worked on timelines faster than most. His insatiable appetite for knowledge and identifying alpha showed me the true ethos of the Bay Area and how the area truly does attract the best talent.
Simona Golebiowska, Leo vonP, Lindsay Hoffman: The can-do team that executed within every role the company needed – and those needs changed quickly! We moved quickly, tried everything and enjoyed the failures and successes. Each brought curiosity and can-do attitude to every growth and operations problem and I loved those days knowing that no mater what came up, this team could handle the attempt. Most individuals cannot match a start-ups fluid needs and this team (and others) handled every turn and speed.
Sai, Jake & Jeff & other eng team: The evolving engineering team had great leaders throughout (Paul Butler, Chris Hanson) and at the end Sai, Jeff & Jake brought all of our various projects and products together. If the first few years were about getting the infrastructure in place, the final 12 months were about increasing monetization. The team’s need in the final 12 months to understand the infrastructure while building applications and products to accentuate growth was stunning. One of my biggest regrets will be not knowing what else this engineering team could have done with another 12-24 months of runway.
Mike Rudolph & Erica Hennes: The marketing team that got it. Over budgets weren’t huge but Mike’s experience and Erica’s hustle seemed to accomplish every task. With Mike and Erica running the marketing group, we had immediate transparency, clear product requirements and a strong backbone to ensure the company was being truthful on expectations. Mike’s direct method of communication and ability to orchestrate multiple campaigns while still diving into the numbers and understand data analytics (with thanks to Michael Michonski!) was exceptional.
David Yi: Epic part time CFO. David taught me a lot about business economics, how to better understand the LTV / CAC trade-offs, how to manage capital raises and how to better manage both being acquired and getting acquired. Every start-up needs a David and we were lucky to have him.
Robin Swanson: The backbone of the Dallas office and a constant reminder to place the customer first. Robin was tireless in her work ensuring our day to day operations remained strong and was the big smile we all needed.