Fund/Build/Scale

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 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.
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, PoshmarkTracy Sun, co-founder, Poshmark
LyAnn Chhay, VP, 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 very soon.
Join the FBS LinkedIn group
Subscribe to Fund/Build/Scale on Substack
Fund/Build/Scale is sponsored by Mayfield and Securiti.

Episode 9 | Taking an AI startup from research to reality with Dipanwita Das of Sorcero

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)
[5:31] Why she interviewed 300+ people to gather insights before Sorcero started building
[6:21] "R&D for us sort of is in two halves."
[8:57] Building a team with the right balance of skills and entrepreneurial spirit
[10:52] "Someone… suggested we use the frame, 'minimum lovable product.'"
[12:20] "My TAM calculation was a bit amateur in the early years."
[16:28] How Sorcero managed R&D while building trust with early customers
[19:14] Series A milestones
[21:44] "I zeroed in on a number of roles" in hundreds of customer discovery interviews
[26:14] How they determined whether Sorcero would be a horizontal or vertical product
[29:31] If you have a cohesive cognitive framework and market proof, you can fundraise
[32:20] Why AI academics/researchers should cultivate "a customer-facing mindset"
[37:46] When making early hires, "you need a builder persona with an incredible drive."
[41:15] The one question she asks in every interview
[42:25] Her advice for AI founders who are trying to raise funds right now
Links
SorceroDipanwita Das, CEO
Walter Bender, CSO
Richard Graves, CCO
What is a minimum loveable product? [Product School]
Funding alert: AI startup Sorcero raised a (mid-pandemic) $3.5M bridge round
AI startup Sorcero secures $10M for language intelligence platform
How Sorcero is improving the accessibility of scientific literature
Thanks for listening!
Fund/Build/Scale is sponsored by Mayfield and Securiti.

Episode 8 | Securiti CEO Rehan Jalil on scaling to $1M ARR (and beyond)

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]
“The only metric is repeatability.” [4:55]
“So we coined the term ‘privacy ops’… we wrote a book on it.” [7:35]
“Teams have to be very much in sync, which means information has to flow.” [10:39]
“By the time you get to MVP, you better have refined this thing. [12:40]
“Before you bring in sales teams, it’s important that you actually have the content for them.” [15:34]
“The bar is very high within the enterprise, and it takes much longer.” [18:29]
“If you don’t start with conviction, don’t do it.” [21:41]
“Find people who have a common interest on the problem that you're trying to solve.” [26:08]
“If they feel like you helped them… they can actually be advocates.” [28:14]
“Just putting things freemium out there doesn’t mean people are going to adopt it.” [30:41]
“Prioritize finding a viable use case and viable product strategy vs. rushing into something.” [32:36]
Thanks for listening! Follow Fund/Build/Scale on LinkedIn and Substack.

Episode 7 | Communicating your vision with May Habib (CEO, Writer) and Gaurav Misra (CEO, Captions)

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]
Writer's original founding "team is pretty together from early days." [5:45]
"In 2020, I don't remember spending a lot of time on the AI behind the AI." [6:11]
When May recognized that she’d connected with investors who shared her vision [8:30]
"The benefit of the full-stack approach is really becoming pretty obvious for people who are spending time with enterprise customers." [12:11]
"I don't see myself as a storyteller, I see myself as decent at picking up signal from noise and explaining that to people." [13:03]
"I do care a lot about design, about brand.... it's always been a very visual company." [16:07]
"If I was just meeting somebody, they got a slightly different deck in the first meeting." [19:06]
"Even ‘til the Series A, I think I looked down on people who were active on LinkedIn." [20:03]
"I think enterprises are getting fatigued." [23:01]
"If it's AI, show, don't tell, because the capabilities are so wild that you can really blow people away." [26:42]
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]
"We talked to a lot of people to help solve that creation problem that we were trying to go after." [36:34]
Why social media is "a really good way to actually test startup ideas" [38:20]
Investors were enthusiastic about shifting strategy, but "the hard part was to convince yourself." [39:55]
"It's really important to have an investor who understands the space inside and out." [41:29]
"The hardest part has been, what do we actually want to do, and what did we see actually working?" [44:35]
"I don't think of myself as a natural storyteller. I think it's something that I had to learn a little bit more of." [47:00]
Why Gaurav is still Caption's 'chief storyteller'" [49:42]
The importance of aligning your overall vision with PMF [51:16]
"As the company grows, the vision does become more and more crystal clear" [52:10]
"Once people try the alternate solution, they should never want to go back to the original." [54:30]

Fund/Build/Scale mini-episode | From seed stage to Series A with Coalesce CEO Armon Petrossian [Part 2]

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]
focusing on enterprise sales from the beginning was a winning strategy [3:40]
"we had an enterprise sales option straight from the beginning' [5:21]
why he hired a full-time salesperson as soon as Coalesce exited stealth [6:52]
how he connected with co-founder Satish Jayanthi [7:22]
coping with imposter syndrome and overcoming the pressure to perform [12:18]
raising a larger Series A than planned led to better outcomes [14:23]
avoid talking to investors until you're ready to raise — then move fast [16:51]
candid advice for anyone who's interviewing with an early-stage AI startup [18:55

Fund/Build/Scale mini-episode | From seed stage to Series A with Coalesce CEO Armon Petrossian [Part 1]

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]
guiding principles for who should — and should not — build in stealth [4:22]
how to manage customer discovery without revealing too much [6:50]
why they used their seed round "to build out the team as quickly as possible" [10:12]
midway through 2022, fundraising dynamics "changed radically" [11:33]
when investors pushed for a Series A, "I was like, that's crazy" [13:05]
starting up in San Francisco when you don't have industry connections [15:52]

Episode 6 | AI compliance and regulation with Laura Bisesto of Nextdoor

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. We talked about compliance, how to recognize when you need in-house help, and the overall importance of planning for worst case scenarios.
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)
don’t wait for lawyers: work on safety and trust from Day 1 (4:44)
how Nextdoor developed and launched its generative AI principles (7:21)
evaluate and reduce risk before rolling out AI-powered features (9:05)
why product teams should oversee risk management (10:54)
"the regulatory environment is evolving" (12:25)
the Biden administration's October 2023 executive order on AI (15:04)
how to position your startup for compliance with future regulation (18:32)
trickery and a lack of transparency can lead to expensive mistakes (22:22)
be careful when sharing user data between different jurisdictions (23:45)
the most common trust, safety and compliance mistakes AI founders make (25:23)
Fund/Build/Scale is sponsored by Mayfield and Securiti.

Episode 5 | Breaking into enterprise sales with Maria Latushkin (GVP of Technology and Engineering, Albertsons) and Jack Berkowitz (CDO, 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)
What one former Fortune 250 software buyer thinks about your GTM strategy (5:52)
How to keep the whale you landed from pulling your boat under (7:33)
What it looks like when a pilot, POC or partnership goes south (8:49)
Customer discovery: “you can talk to me, but don’t sell to me.” (10:55)
Enterprise software buyers already know your tech isn’t “bulletproof” (12:59)
Red flag: don’t talk to customers like they’re investors! (14:21)
“How can I get that domain expertise before I show up to that buyer?” (16:56)
Partnerships, intellectual property, and procurement for AI startups (20:23)
Turning a pilot program into a long-term contract (23:26)
Proof of concept, opportunity costs, land-and-expand strategies (27:09)
Managing pilot programs and prioritizing one-off feature requests (29:18)
Common mistakes founders make while spinning up their sales motion (31:33)
How success fee agreements work (35:50)
 
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.

Episode 4 | Fundraising from both sides of the table with Jorge Torres (CEO/co-founder, MindsDB) and Vijay Reddy (AI Start investor, Mayfield)

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)
Vijay: "We don't do spray-and-pray." (4:06)
Founders need to de-risk themselves before pitching (5:21)
Jorge's three key questions for early-stage teams (7:14)
Why you don't need a demo, customers or revenue to pitch (9:59)
Founder red flags that turn off investors (14:12)
How to recognize seed-stage investors who actually add value (15:55)
When it comes to accepting early funds, be strategic (18:43)
Don't focus on TAM, just find clear pain points in large markets (22:03)
"If you're close to something that makes sense... don't wait too long to show it to an investor."
(23:41)
How early-stage AI startups can avoid extinction-level events (25:44)
You can't build a strategic moat without real-world data (27:55)
Technical founders should team up with nontechnical co-founders (29:56)
Closing a seed round: how long should it take? (31:32)
How much runway does an AI startup need? (34:05)
 
Links:
Jorge Torres, CEO, co-founder, MindsDB
Vijay Reddy, AI Start investor, Mayfield
MindsDB AI Collective, San Francisco, CA
Mayfield AI Start Seed Fund
aistart@mayfield.com
 
Fund/Build/Scale is sponsored by Mayfield and Securiti.

Episode 3 | Tapping into the AI Developer Community with Ozzy Johnson (Director of Solutions Engineering, NVIDIA)

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)
How AI is leveling the playing field for non-technical founders (4:28)
How to (and not to) recruit talent from the developer community (7:26)
The dangers of digging your moat too early (9:41)
Finding scalable problems customers want solved (11:30)
Prioritize early spending on "saleable differentiation" (14:36)
Top traits of successful AI founders (17:21)
Benefits of NVIDIA’s Inception program (22:11)
Balancing customer feature requests with roadmap control (25:21)
Why the rise of Gen AI is a transformational moment (28:21)
Ozzy’s advice for anyone interviewing at an AI startup (31:36)
Thanks for listening!
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