Episode 10: Two repeat founders share long-term strategies for building sustainable startups

The average failure rate for a tech startup is 90%. 

Around one-fifth will flame out in the first year, and the overwhelming majority of the ones that make it past that mark will never be acquired or go public. It’s brutal.

It takes years to build a sustainable technology company, and considering how unbalanced the risk/reward ratio is, each founder needs to craft personalized mental and emotional frameworks that suit their needs.

Because there’s no single recipe for long-term success, I was glad to interview Poshmark CEO Manish Chandra and DevRev CEO Dheeraj Pandey about how they deal with the fear, uncertainty and doubt that follow every entrepreneur.

"By the way, the only job of the CEO over time is to go towards the fire."

Poshmark is a pure consumer play, and DevRev sells enterprise software, but because Dheeraj and Manish are repeat founders who’ve taken startups from Day Zero to IPOs, they were an excellent choice for the last episode of season 1.

We broke down some of the strategies they’ve developed over time for recruiting, fostering early adopters, driving growth, and transitioning across industries. Both guests also unpacked some of the strategic decisions that propelled their companies forward and spoke openly about how they navigated some very lonely times along the way.

“Whatever you don't have, you can always find it in someone else.”

Episode breakdown

• [2:38] Dheeraj: “The hardest thing was to really find the innovators and the early adopters.”
• [4:40] Manish: “I just kept saying, ‘I'm not the right guy to do this idea because I had no consumer background.’”
• [7:03] Why it’s so important to build an advisory team early on
• [8:12] Dheeraj: “Finding people who have hunger and humility… has always been hard.”
• [10:51] Prioritize hiring early employees who will challenge you and your assumptions
• [14:18] Use your initial recruiting process to refine your value proposition
• [17:30] When Manish realized Poshmark was the right company for the moment
• [21:24] Winning “VMworld awards basically told us that we're doing something right.”
• [24:36] Manish: “We got the first version of the app ready, but there were a couple of problems.”
• [30:09] Dheeraj: “We said, ‘we’ve got to take something to the have-nots.’”
• [35:14] Embrace a design-first mentality from Day Zero.
• [39:00] Search for ways to reduce friction from every internal and external process
• [43:21] Dheeraj: “By the way, the only job of the CEO over time is to go towards the fire.”
• [50:39] When it comes to design, “less is better”
• [53:39] Manish: “Whatever you don't have, you can always find it in someone else.”
• [55:16] Dheeraj: “The more and more money you actually raise, the less you can pivot.”
• [59:21] Manish: “Always be closing, because money can disappear very quickly.”
• [1:02:32] Dheeraj: “I think my learnings have been about keeping the balance sheet in your head all the time.”
• [1:05:31] How to recognize when it’s time to throw in the towel
• [1:07:01] Is work-life balance even an achievable goal for an early-stage founder?

Links

• Manish Chandra, CEO, Poshmark
• Dheeraj Pandey, CEO, DevRev
• Kaboodle
• Nutanix
• TiE Global
• Gokul Rajaram on Twitter: “VISION => TALENT => TEAM”
• What Is Forming, Storming, Norming and Performing?
• How to Be a C.E.O., From a Decade’s Worth of Them
• Rise of Empires: Ottomans
• Eclectic grandpa style
• Simon Sinek

Thanks very much for listening to season 1 of Fund/Build/Scale! There’s much more to come in season 2, which starts soon.

Fund/Build/Scale is sponsored by Mayfield and Securiti.