March 14, 2022 | 6 minutes read

From Sports to Startups

Owner, GM, Coach, Player: The Many Hats a Founder Wears

Dan Sahar
Co-Founder and CEO of Guidde

Everyone knows that a startup is a roller coaster, but to me as a repeat founder (currently now the co-founder and CEO of Guidde), the most thrilling times were the first couple of years going from an abstract idea to a product with actual customers. It’s not that the excitement subsides later, it definitely doesn’t, but those first couple of formative years have the most “unknown unknowns” (biggest questions), decisions that have the most long-lasting impact (think product architecture), and a full matrix team where everyone still knows everyone (even the sales reps know names of the engineers).

While these early days are the most exciting, they’re usually also the most stressful and challenging to navigate for any entrepreneur (both first-timers as well as those on their second or third rodeo). One of the key challenges is that it’s the period where founders wear the most “hats” in the startup journey. 

During the course of a single day, a founder may write code, develop a new guerilla marketing campaign, try to recruit a new hire, and onboard a new member of the team, while trying to close a design partner that’s been impossible to reach, and finally doing a quick zoom with an angel investor you just got introduced to. These early days are hectic. 

If we would compare the world of startups (one of my favorite worlds) to my second favorite (the world of sports), all at once, a founder shapeshifts between an owner, general manager, coach, and player. When you think about it,even doing two of these things at once on a sports team is a stretch – think of any player/coaches or coach/GM combinations in any sports team and the successes are rare and far between. (The only successful example I can think of is Jackie Moon who was ​​ the owner, head coach, starting power forward, and pre-game announcer of the Flint Tropics.)

So why does this “many hats” situation happen with startups when its proven not to work with other team initiatives like sports? And what tips can we take from the sports world into the startup world to empower our future startup teams to win our versions of the World Series, Championships, and Super Bowls? 

🧢 Tip #1: Release some hats

For the formative first year of your startup, you’ll probably have to carry some combination of the various roles. However, as the company progresses, it is critical that founders resist the temptation to hold on to roles that are dear to their hearts (even if you pride yourself as a crack coder or think you can close deals better than your best AE), and hand over the reins to department leaders and individual contributors in your team. 

The “player roles” I’d look to hand over first, would be roles that are more internally focused like writing code, while roles that have direct interaction with customers, I’d hand over last. The direct interactions with the field are crucial in finding your PMF as well as having a deep understanding of the problem domain and fine-tuning the message and story accordingly. By having a sales proxy to the field too soon, founders often lose the soft signals that can only be learned on live calls and meetings with prospects and the field. 

🤼‍♂️ Tip #2: Hire the best coaches

Coaching in a startup mostly resembles coaching in American Football. Similar to football where offense, defense, special teams, receiver, QB, linebackers, and more each have their own coaching staff, in a tech company, R&D, Sales, Marketing, Customer Success, Finance have their own coaches. Founders may be one of these coaches in the beginning (and in some cases throughout the lifetime of the company) but most of the coaching roles are going to be filled by non-founders over time. The role of the CEO becomes similar to the “coaches’ coach” providing strategy support and guidance to each individual department coach and often serving as a sounding board and coordinator between the various teams.

📑 Tip #3: Build up a solid roster

Rather than coaching, to me, the most important role and the one you want to dedicate most of your time and energy to as a founder is the role of the team’s General Manager. In basketball teams, the GM’s key responsibility is roster construction. They are in charge of signing players, making trades, and selecting draft picks. Basically, they decide who’s on the team. In a sports team, the composition of the team often dictates the style of play and has to be part of a broader strategy –the players have to fit the vision of the GM where the goal is winning a championship. For example, if the GM (with the consent of the owners of course) believes in a “7 Seconds or Less” run and gun offense, then they better hire both personnel that can execute it (think Steve Nash and Amare Stoudamire) but also a coach that can put that plan into action like Mike D’Antoni.

During that first year of existence, I think the best model to take is the roster construction of an expansion team. In most North American leagues, new teams are added every several years and have to start pretty much from scratch. – The most recent example is the Las Vegas Golden Knights that reached their Stanley Cup Finals in their first season of existence. 

The Knights managed to build a roster combining several savvy veterans; in our case, think of your startup roster including a couple of developers with 5-10 years experience that are self-sustained on their own, combined with a whip-smart system architect that is a builder, hungry department heads that have proven themselves and want to lead, and finally sprinkle in a few rookies fresh out of college that may cause you grief from time to time in the beginning, but will reap you massive dividends down the road, (and bring in some good vibes and casual mayhem that will keep the team on their feet in a good way).

🎨 Roster construction is an art

It is probably the most important and challenging task you’ll have as a founder/GM. The quality of the team you constructed will have an outsized stake in the outcome of your venture and will dictate how you navigate as a group through the good, bad, and odd times that are bound to happen at some point – no pressure. 

If you recruit well, every once in a while you may find your Dirk or Van Vleet, those hidden treasures that no other company understood their value but at your company became superstars. Of course, you’ll make some mistakes – just make sure to trust your gut on this and correct them quickly. 

And at the end of the day remember – don’t be too hard on yourself. Know this – even the great ones are just riffin’, baby*.