In this week’s episode of NY Seed Round, host Justin Wolz sits down with Rob Bailey, co-founder of CrewAI and a veteran of the startup space as both a co-founder and advisor.
Rob rose to prominence by playing a huge role in scaling Kustomer, which was eventually sold to Facebook for a billion dollars. As a result of that exit and his wide variety of experiences since, Rob has learned quite a bit about what makes founders truly successful.
In this episode, Rob dives into tons of actionable insights for founders, including:
For all of Rob’s perspectives, be sure to check out the full conversation with host Justin Wolz.
Below, we’ve shared some notable insights Rob shared during their conversation.
One of the biggest mistakes Rob sees founders making early on is not talking to nearly enough customers. But when they do, they typically focus on talking to customers that are too big or too small.
"I found that frequently, the very technical founders like to talk to individual developers and small customers, and that can be not representative of where the revenue opportunity is. I also find that founders will frequently get enamored with the really big names," said Rob.
Instead, Rob recommends a more balanced approach: focusing on businesses he calls "tunas" with anywhere from 50 to 250 employees.
What I'll typically recommend to founders is almost like a portfolio approach of your customer base and time.
Identify your whales and go after them, but you should be spending the majority of your time going after customers that can close faster.
This allows you to make big bets while also keeping your traction going with smaller prospects with the ability to move significantly quicker than larger businesses.
Based on his experiences, Rob noted that the best founders he’s come across all had one shared trait: speed.
I would say probably the most interesting thing in common threads that I've seen across exceptional founders is their iteration speed.
For Rob, how they observe and adapt to the current state of their business and how they action data and evolve based on metrics are all telltale signs of a 99th percentile founder.
“When I look at the best-performing investments that I've made in early stage founders, that was very clearly a common characteristic.”
As an early-stage founder, once you secure a few investments, it can be tempting to lean a bit too heavily into the guidance you get from investors. But while Rob doesn’t recommend you completely ignore all wisdom from your investment team, he does suggest being a bit more comfortable in knowing when to lean in versus making your own calls.
“I think it's really important for founders to develop their own sense of decision-making and judgment," said Rob.
And a mistake that I frequently find founders making is being overly reactive to advice and suggestions from their investors.
For Rob, it starts with being strategic about the investors you do pick and understand what each of them bring to the table. But when it’s time to make decisions, don’t be reactive for sake of it—develop your own intuitions and let them guide you when necessary.
“So it's really [about] developing your own unique, but really smart point of view. That's constantly evolving rather than just reactively doing whatever, you know, some investor may have suggested off the cuff.”
Note: This content is for informational purposes only. It doesn't necessarily reflect the views of Rho and should not be construed as legal, tax, benefits, financial, accounting, or other advice. If you need specific advice for your business, please consult with an expert, as rules and regulations change regularly.
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