Fund/Build/Scale Walter Thompson

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]

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

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]

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.

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.

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.