Helping founders since back in the day
The most rewarding part of my career has been helping founders to build companies. It’s easy to be cynical about the startup ecosystem, but, for me, the idea that a small band of people comes up with and then executes a plan to build a giant company remains truly magical.
I spent the first 20 years of my career helping founders navigate this journey as a lawyer. In this role, I was a part of many critical moments in a company’s life: formation, financings, board meetings, acquisitions, and in a few cases the IPO. It was wonderful, and I learned so much by watching what made companies like Facebook, Square, Dropbox, and Zuora succeed. I moved into seed investing to see if I could pick a handful founders with whom I could share all of these learnings. For more than 5 years at Cowboy, I’ve had the pleasure of helping a small group of smart, hardworking and determined entrepreneurs grow their businesses. I also learned from my brilliant partner Aileen Lee how to think like an investor. For that, and a whole host of other reasons, I’m eternally grateful to her.
When the time came to sign up for Cowboy’s 4th Fund, however, I concluded that being a seed investor in today’s market required a time commitment that was incompatible with certain of my family obligations. Accordingly, I have transitioned to Board partner at Cowboy where I can focus my energies on helping Cowboy portfolio companies thrive.
I’m starting something new.
While I’m excited about the work I can do with Cowboy companies, I also want to devote more time and attention to the thing that I like best: helping founders grow their businesses. Accordingly, I’ve launched a coaching business called Stoked Advisors. My goal with Stoked is to help companies in the same way that I have helped Cowboy portfolio company founders, by being a trusted business advisor with whom they can work on their most important problems.
What kind of coaching?
Stoked is a business coaching service which provides founders a trusted advisor to talk through and improve on their ideas for growing their business. While investors and other board members are tasked with assessing the performance of a founder for future funding and continued leadership responsibility, Stoked’s sole focus is to provide targeted feedback on how a founder can improve. The advice is based on working with thousands of companies over 25 years and understanding what tactics and strategies have helped make companies successful (and which ones have not).
When founders are looking for advice there are typically a couple of different sources:
Executive coaches, who can greatly help the founders understand themselves and their context, but generally avoid directly advising on the substantive business issues the founders are tackling.
Successful current and former operators, who help on issues like go to market or engineering, but typically have only the data points of their own experiences and/or have a more narrow area of expertise; and
Investors, who often have the broad pattern recognition, but whose interests can create a difficult environment for vulnerability and honesty with founders.
Stoked is designed to bridge this gap in the market, giving founders someone in their corner who has worked with a wide range of companies over many years, but is not deciding whether to invest in a follow on round or replace the founder with a more seasoned manager.
What is the service?
From a coaching perspective, I am more like a college basketball coach than a youth coach at the local YMCA. I focus on the small corrections that can separate great from good, as opposed to the teaching the fundamentals. A good example of this is how I help with fundraising.
There are millions of sources of information about the basic elements of fundraising (e.g. the elements of a pitch deck, the different types of investors and rounds, etc..). I try and help with the more nuanced elements of the fundraising process, such as, telling the story in the most compelling way, managing the process and impressing the investors outside of the actual pitch. My time in the ecosystem has given me a good sense of the differences among various investors. An approach that is spot on with one investor may be a total fail for a different investor.
My Cowboy portfolio companies have told me that this type of coaching has been incredibly valuable, even for founders that have raised many rounds in the past. It’s an area where small modifications can have a big impact in result.
Other examples the types of things I can help with are:
recruiting a great team:
setting and strategic priorities and managing to them; and
communicating succinctly and appropriately with investors and the board.
While there is much written on all of these topics, the real value is helping founders apply the general principles to their own circumstances. 20 time Grand Slam winner Roger Federer has a coach….for tennis. For even the most experienced founder, having a second set of eyes on their work can have tremendous value, particularly in some of these high stakes area. To quantify it, a 10% improvement in a fundraising outcome could add millions of dollars (and months of runway) to a company, and I try and target the work on these high leverage areas.
Why Stoked?
Startups are REALLY hard. The name Stoked is an effort to capture the relentless positivity I try to introduce into the daily grind. That said, if you are looking for a cheerleader and equate “founder friendly” with only giving positive feedback, I am not your person. I view feedback as a gift and believe in radical candor so I pair best with folks who appreciate that approach.
Stoked also describes the type of founder with whom I want to work. While the word “stoked” carries some surfer-bro connotations, in my experience the most stoked founders are introverts who quietly go about their work, passing on their infectious passion and enthusiasm without crowing or beating their chests. One of the great joys of my time at Cowboy has been working with Anna the CEO of Uno Health, who is driven to improve healthcare outcomes, but seems unlikely to be starring in a remake of Point Break.
Some example engagements
My initial Stoked customers (outside of Cowboy) are Ironclad, Satellogic and a yet to be launched healthcare company lead by John Haskell. John has set out to build a company focused on improving outcomes for kids with severe mental illness, something near and dear to my heart. I’ve been working with the him on assembling the right team and fundraising. With Ironclad I am doing some general business coaching in addition to some deeper projects on equity compensation and features for the Ironclad community. For Satellogic, I’ve been serving on the board of directors, helping them to recruit a public company board and navigate their recent SPAC and PIPE transactions. What’s drawn me to each of these engagements is a visionary founder of a mission driven company who is looking for candid feedback informed by experience and good judgment.
If you are a founder that is genuinely passionate about what you are building and thinks you could benefit from an energetic, experienced, and opinionated advisor, I would be stoked to meet you. Give me a shout!