Fund/Build/Scale

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 affects every entrepreneur.

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.

• [2:38] Dheeraj: “The hardest thing was to really find the innovators and the early adopters.”

• Manish Chandra, CEO, Poshmark
  • Tracy Sun, co-founder, Poshmark

Thanks very much for listening to season 1 of Fund/Build/Scale!

There’s much more to come in season 2, which starts very soon.

• Join the FBS LinkedIn group

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

For this episode of Fund/Build/Scale, I interviewed Dipanwita Das, CEO and co-founder of Sorcero, about the journey of taking an AI startup from research to reality. She shared her experience of interviewing more than 300 people to shape Sorcero's product and technical requirements, as well as strategies for aligning customer needs with product development. We also discussed the challenges of building a capable team, fundraising, and the process she and her co-founders used to transform their thesis into a marketable product.

• [1:55] How Sorcero’s co-founders connected and launched in 2018 (before the AI boom)

• Sorcero
  • Dipanwita Das, CEO

Thanks for listening!

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

Going from zero to $1M in annual recurring revenue is worth celebrating, but it’s no guarantee that your startup is on a path to success.

How long did it take to reach this milestone? How much did you spend to acquire each customer, and how many have renewed or extended their contracts?

When it comes to sales, repeatability equals success. To learn more about the tactics startups use to reach $1 million ARR (and beyond) I interviewed Rehan Jalil, CEO of Securiti.

Drawing from his experience as a three-time founder, we talked about setting up an initial sales motion, understanding and validating the problem you're solving, focusing on a specific audience to hone your value proposition, and building trust with early customers.

Episode breakdown:

• “Before we even get to the revenue, it actually is important to understand what problem you're trying to solve.” [2:10]

Thanks for listening!

Successful entrepreneurs must translate their personal visions into something tangible enough to attract employees, investors, and eventually, customers. 

There are best practices for product management and software pricing, but how do you make yourself persuasive (and authentic) enough to convince someone else to risk their time and money on your idea?

I interviewed May Habib (CEO and co-founder, Writer) and Gaurav Misra (CEO and co-founder, Captions) to learn how they use a mix of hard and soft skills to maintain a clear and strategic vision that informs everything from recruiting to GTM strategy. 

We also discussed methods for finding investors who understand your space, building a team, and why “rarely is the first idea the right idea.”

Here’s a full episode breakdown:

Part 1: May Habib, CEO and co-founder, Writer

• "This was going to be just a much more interesting product." [03:27]

Part 2: Gaurav Misra, CEO and co-founder, Captions

• "We want to come up with a lot of different ideas in this space and what gets us excited." [33:32]

In part two, Armon explained why he initially resisted investor advice to raise a Series A and spoke frankly about the challenges involved with stepping up into a leadership role, which led to some interesting talk about overcoming impostor syndrome, something a lot of us can relate to.

Part 2:

• show Series A investors market opportunities you've already validated [1:51]

I interviewed Coalesce CEO and co-founder Armon Petrossian in February 2024 to talk about his company's journey from seed stage to Series A. I had no idea he was already working on his next round: just a few weeks after we recorded this interview, Coalesce announced a $50M Series B.

To help me prepare, his team shared their slightly redacted Series A pitch deck, which was immensely helpful. I'd intended to make this a mini-episode, but there was so much here, I decided to break it up into two parts.

Part 1:

• why building in stealth was the right call for Coalesce [1:39]

I interviewed Laura Bisesto (global head of policy and privacy at Nextdoor) in January 2024 to get her advice for AI startups that are just starting out.

She also had some thoughts for rolling out new AI-powered features, creating user advisory boards, and navigating a patchwork of state, federal and international laws.

Here’s a breakdown of our conversation:

• “You don’t have to be an ethicist to start an AI ethics program..” (2:44)

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

For episode 5, I interviewed Maria Latushkin, GVP of Technology and Engineering at Albertsons, the second-largest grocery chain in America, and Jack Berkowitz, Chief Data Officer at Securiti (previously with ADP), to get their insider's perspective on how enterprise-level customers buy software and services from AI startups.

The most surprising thing I learned came early in the chat: spinning up a pilot program or a partnership creates tangible risks for enterprise customers, which means they can only afford to work with a few startups at a time.

Maria and Jack each have startup experience, but their time as C-level execs inside public companies gives them a unique perspective on breaking into enterprise sales. 

In this episode, we'll talk about sales strategies, navigating the procurement process, how to run a proof of concept or pilot program, and other essential topics.

Here’s a full breakdown:

• The challenges and rewards of being an early-stage company's first customer (3:00)

For my next episode, I spoke to Laura Bisesto, global head of policy and privacy at Nextdoor. 

We talked about the regulatory landscape facing AI startups in 2024, and how small companies should start the work of developing their own ethical frameworks. We got into how to recognize when you need legal help, recapped some data governance best practices, and also talked about why it's so important to create a buttoned-down process for rolling out new AI features.

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

Jorge Torres (CEO, co-founder, MindsDB) and Vijay Reddy (AI Start investor, Mayfield) were the first two people I interviewed for Fund/Build/Scale. 

We met up at Jorge's office in San Francisco's Mission District on a rainy Friday afternoon in November 2023. We spent time discussing the ins and outs of pitch tactics and investor outreach, but we also talked about the criteria VCs use to evaluate zero-day investments, which red flags investors and founders both need to look out for, and how to find a VC to partner with for the next decade (not just the next funding round). 

Jorge has been through the fundraising process three times and Vijay is an experienced seed investor, so I was glad to talk to them both about fundraising from both sides of the table.

Here's a breakdown of our conversation:

• How Jorge and Vijay assess team quality (2:28)

Links:

• Jorge Torres, CEO, co-founder, MindsDB

• [email protected]

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

I wanted to learn more about how inception-stage AI founders can tap into developer ecosystems, so I spoke to Ozzy Johnson, Director of Solutions Engineering for NVIDIA Developer Programs.

In his role, he leads a global product team that accelerates its own work by interacting with outside developers who use the company’s technology. Johnson also works with NVIDIA’s Inception program, a virtual accelerator for AI and deep-learning startups.

“It's kind of necessary to know the shape of the world to have a sense of where things are headed,” he said.

“We ideally want to see around corners, we want to try to get there first, or at least, meet developers where they are.”

Here’s what we talked about:

• Why more AI founders should focus on fundamentals (1:50)

Thanks for listening!

Fund/Build/Scale on LinkedIn