Issue #34: Five themes from a founders summit

I spent most of Sunday at a founders summit that Ezra Galston of Starting Line organized in Chicago. While Cargado is not in Starting Line’s portfolio, Ezra has been an angel investor in both Forager and Cargado and has been an awesome supporter of my entrepreneurial career so far. I was fortunate to have a chance to attend this weekend’s event and meet and learn from some incredible entrepreneurs, operators, and investors.

Here are five themes I heard that I want to share with other founders and operators:

Hustle non-stop

We heard from a trio of early operators who had been at DoorDash, Instacart, and WeWork. They talked about what the environment was like at each startup and the theme that rang true throughout the whole conversation was the need to move fast and hustle. If you aren’t willing to grind it out and do whatever it takes to build a startup, then it might not make sense to sign up and work at a startup. There were young people in roles for the first time, potentially new roles that weren’t replicated from other businesses (like the community manager role at WeWork) and you had to just figure it out.

Building for scale

Building a team that can scale with a rapidly-growing startup can be incredibly difficult. When you hit rocketship speed, hiring seasoned execs – “grey hairs” as most VCs call it – is not a certain path to success. It’s incredibly important to make sure that these seasoned leaders, if you do hire them, are willing to roll up their sleeves and actively do the work themselves. If you hear them asking about hiring VPs and Directors right out of the gate, think twice before hiring that person.

Choose your investors carefully

Not every VC investor is a great board member. When you’re building a venture-backed startup, you need to be intentional about the investors on your cap table. If you’re building a startup for the first time, you likely haven’t seen what it looks like to scale a great company from the executive level, and you likely haven’t seen the miserable side of the spectrum that most founders want to avoid. The right board member has seen it all and can partner with you to help avoid some of those potential pitfalls.

When you take a call with an investor, you’re fundraising

Any time you take a call with an investor, you’re pitching them. Whether you have a formal deck or you just casually tell them about your company, it’s a pitch. Don’t take the calls if you aren’t prepared to pitch as the first impressions can be meaningful. And focus on taking meetings with people who can actually write checks.

Great founders sell the vision

I heard this same concept from a founder, from the three operators, and two venture capitalists: great founders are always selling the vision and setting the tone for the culture of the company. Whether that non-stop hustle manifests itself in a founder doing demos for prospective customers all day long or diving deep into the code themselves, the great founders will grind it out with the team and help them all scale with the business. They make sure every single person on the team understands where the company is going and what the grand vision is. It’s almost an expectation more than a dream that you’re going to achieve that vision and you have to act accordingly to do so.

If you get an opportunity to attend a founder summit and build relationships with other founders, take advantage of it. It can be an incredibly fun and rewarding experience to spend the day dedicated to good discussion and not staring at your phone, even when news breaks mid-day that rocked everyone’s Sunday.