The Founder Playlist: Reflections on Really Good Advice from 45 CEOs

Leading a company as a founder and CEO can be exhausting. Between fundraising, hiring, listening to customers, and building products, it’s tough to make room to seek out advice from other experienced founders –– even when you know it’s valuable. As challenging as it might be to find the time, there’s no reason to make the same mistake twice when you can learn from other founders who’ve been there and done it before.

I’ll never forget when, as a first-time founder, I implemented a sales commission plan that almost bankrupted my company. I crafted the plan without consulting with any veteran sales leaders and without considering how the possible scenarios could play out. I’ll never make that misstep again, but I wish I’d asked for counsel in the first place from someone who could have prevented my sloppy mistake.

Our team developed the Founder Playlist with the aim of making startup advice from accomplished leaders accessible to everyone — a playbook for how to build an early-stage startup and grow as a leader.

When we first embarked on this project, we were taken aback by how many founders swiftly agreed to participate. It quickly became clear how many founders were eager to share what they wish they had asked someone at the start of their own founder journeys. In total, more than 45 founders and senior leaders participated, offering 475 short audio and video clips of advice.

It’s probably time to face the fact that you will never read that stack of leadership books on your shelf; you’re just too busy. Everyone is pressed for time these days and we’re increasingly wired for shorter bursts of information, so we cut straight to the essentials. Imagine your favorite podcast, but just the golden nuggets of advice you want to highlight from each segment.

After listening to all the featured founders share their advice for fellow founders, three key themes stuck out to me.

Building Healthy Co-Founder Relationships

According to HBS Professor, Shikhar Ghosh, only 25% of startups survive, often due to unhealthy co-founder dynamics. Before you rush into choosing a partner, it’s critical that you spend time thinking about your own mission and values, which complementary skills you need in a partner, and the qualities you’re seeking in a co-founder.

In the Co-Founder Relationships playlist, founders like Brian Halligan (CEO, HubSpot), discuss why having defined roles among co-founders is key to success. Halligan shares that he knew that his co-founder, Dharmesh Shah, was the one when he realized they had complementary skill sets in sales and engineering. In the same playlist, other founders discuss how they quickly learned the 50/50 equity splits with co-founders didn’t make sense, and tough lessons learned about what happens when a company doesn’t work out.

Navigating Investor Meetings

For many founders, one of the most stressful hurdles to surmount is raising the capital you need to get started –– crafting your story, building a target list of investors, navigating investor meetings, and negotiating term sheets. In the Fundraising playlist, Steve Kokinos (CEO, Algorand) emphasizes that it’s ok to say you don’t know the answer to a potential investor's question. In fact, it creates trust and builds confidence through transparency, as long as you follow up by refocusing the conversation on where you want it to go. In conjunction with admitting what you’re still figuring out, project how you have command of the business such as how you’ll grow, scale, understand the market, and what challenges you’re solving.

Fellow Pillar Partner and former E Ink CEO, Russ Wilcox, articulated that it’s important to keep in mind how an investor is evaluating the company, including whether the opportunity fits their investment scope right now and whether you could see yourself spending a decade collaborating with the founder.

Investing in Your Mental Health

When you’re pouring your life into building a company, it’s essential to take time to invest in your health and mental wellness. It’s so easy to kick this item to the bottom of the to-do list when you have some many competing priorities, but the reality is that if you want to take care of your team, you have to start by taking care of yourself. It’s not an indulgence; it’s an investment in your company. Steve Conine, Co-Founder of Wayfair, shares in the Founder Playlist that when you step back with a clear perspective, even the worst-case scenario often really isn’t that bad. Steve also suggests that a durable business is one that is set up so you can take some time off; a business that is run like a sprint isn’t really sustainable in the long run.

The reality is that the founder journey is incredibly hard. While it can be energizing, it can also be lonely and isolating –– you’re often on an island of one. One of the best things I can recommend to any founder is to build relationships with other founders, on your own or through a CEO group, who you can confide in and who can offer support and a sounding board.

Amy Villeneuve of Amazon Robotics (Kiva Systems) articulates this best, "Founders tend to discover early that it is lonely at the top. You bear the weight of the company as soon as you hire your first employee. Having access to advice from others who have gone before you, is invaluable.”

While you might feel like the only person in the world experiencing a rough patch, as soon as you start to talk to your peers, you begin to realize that you’re not alone.