Fund/Build/Scale

Leveraging Founder-Market Fit to Win Over Risk-Averse Buyers

What happens when a team of legal veterans decides to rebuild the dispute resolution process from the ground up? 
To find out, I interviewed Rich Lee, co-founder and CEO of New Era ADR, a platform designed to resolve legal disputes faster, at lower cost, and with less friction for both companies and individuals. 
We talked about building a team that had enough credibility to sell into one of the most risk-averse industries, how they approached trust-building with both customers and investors, and how they're scaling a capital-efficient business in a category that’s been largely unchanged for decades.
Thanks for listening!
– Walter.
RUNTIME 39:46
EPISODE BREAKDOWN
(2:59) “ I'm an early adopter of, you know, anything.”
(10:03) “ The core problem: why does it cost so damn much to resolve a legal dispute in this country?”
(13:05) How Rich and his co-founders divided roles and responsibilities
(17:15) Hurdle #1: “ Challenging the underlying assumption that litigation and a legal dispute doesn't have to be two-plus years.”
(22:32) In the early days, New Era ADR developed multiple personas to overcome customer objections
(25:50) “ Fortunately, we didn't have to do a lot of POCs.”
(29:40) “ Our market's comically big.”
(30:03) Finding your SAM and SOM when the TAM is $350 billion
(32:22) Which came first: the pitch deck, or the revenue model?
(35:50)  One question Rich would have to ask the CEO if he were interviewing for a role with an early-stage startup.
LINKS
Rich Lee
New Era ADR
The Future of ADR? New Era Bags $6.3m While Still at Seed Stage, Artificial Lawyer, 3/16/2022
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From Side Project to API Powerhouse: How Postman Went Global

Before Postman became a category-defining platform used by millions of developers, it was a personal side project. In this episode, co-founder and CEO Abhinav Asthana shares how he went from hacking on API tools in Bangalore to leading a global company with nearly 900 employees across three continents.
We talk about:
Building a developer-first product that spread through word of mouth
Choosing a CEO when everyone on the founding team is an engineer
How to reach U.S. customers before you have a U.S. presence
Why authenticity beats thought leadership when you're building in public
Going from “ramen profitability” to Series A in just 17 months
Whether you're an engineer who’s thinking about starting something of your own, a founder operating outside of Silicon Valley, or just curious how Postman actually works, this episode is packed with tactical insights.
RUNTIME 49:19
EPISODE BREAKDOWN
(2:39) “ Being a developer who loved to hack and also design, I just decided to try my hand at this.”
(4:00) “ We had a hypothesis, but we didn't have a company.”
(6:08) Abhinav built goodwill with the developer community by being helpful
(9:26) How they settled on the name “Postman”
(11:51) On a team of engineers, how do you decide who should become CEO?
(15:00) Who was their first key hire outside of the founding team?
(20:15) Why he thinks early-stage startups should seek “ramen profitability”
(23:23) “ Our first marketing hire was about two years in.”
(25:18) What it was like to go from a seed round to Series A in just 17 months
(30:02) “ At that point, it kind of became clear that this is a new kind of category.”
(32:15) How Postman’s branding dovetails with the platform’s underlying technology
(36:13) One thing he would have done differently in the run-up to the Series A
(38:48) Managing cross-border growth when you’re based in Bangalore
(40:56) “ Building the company in two different places… it's just incredibly hard.”
(44:47) “ Don't skimp on two things ever in starting a venture-funded company: your lawyer, and your accountant.”
(45:52) One question he’d have to ask the CEO if he were interviewing for a job with an early-stage startup.
LINKS
Abhinav Asthana
Postman
Postman raises $50 million to deliver its API collaboration platform to more partners, 6/19/19, VentureBeat
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Thanks for listening!
– Walter.

When a Power User Becomes CEO: How Medium Found Its Way Back

When Tony Stubblebine took over as CEO of Medium in 2022, the platform was burning $2.5 million a month, bleeding subscribers, and was overrun with content that left founder Evan Williams cringing. 
Tony pitched Ev a turnaround built on small teams with access to data, customers, and the freedom to rebuild Medium like a startup from the inside out.
He wasn’t just another executive parachuting in — Tony had worked with him as head of engineering, later as a power user and publishing partner, and eventually, the person who convinced Ev that he could get things on track.
In this episode of Fund/Build/Scale, Tony explains how Medium became profitable for the first time, why the platform banned AI-generated content from its partner program, and how his long history as a user and advisor uniquely prepared him to lead the company through a delicate transformation.
RUNTIME 50:14
EPISODE BREAKDOWN
(3:41) “ I have a long track record of being associated with Medium for just strange reasons.”
(7:16) “ Maybe I'm crazy, but I thought on day one, ‘oh, this is a guaranteed win.’”
(9:52) “ I think CEOs are delusional, and some amount of delusion is probably healthy.”
(12:34) “ Precision is not possible without a combination of data science and user research or words.”
(14:30) Creating customer feedback loops in a 13-year-old company
(19:49) “ I would almost say there's no product to manage yet because we’re making it, and we’re making it together.”
(20:17) The two mandates Evan Williams gave Tony when he hired him as CEO
(24:23) “I  knew even if we could grow subscribers, it would be on the back of this content that we weren't proud of.”
(25:45) Why Medium banned AI-generated content from its partner program: “ We're a pro-human product.”
(30:11) “ We love human moderation. We love our trust and safety team.”
(36:28) “ We're trying to be a place where a different set of writers will win on Medium than will win on these other platforms.”
(40:46) “ One hundred percent: Medium is for experience, not for influencers.”
(42:35) “ I really like to be a champion for what I would call ‘white hat content marketing.’”
(46:45) “ It's wild to me that the art of blogging has not been perfected this many decades into it.”
(48:17) “ It's impossible to understand how many niches there are.”
LINKS
Medium
Tony Stubblebine
Tony’s Medium profile
Mark Suster
Cal Newport
Flow: The Psychology of Optimal Experience, Mihaly Csikszentmihalyi
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Thanks for listening!
 
– Walter.

Muse Capital’s Approach to Finding Value in Overlooked Markets

Rachel Springate is the founding general partner of Muse Capital, an early-stage venture fund focused on overlooked sectors like women’s health, wellness, parenting, gaming, and sustainability.
In this episode, she shares her strategy for finding value where other investors aren’t looking, explains how Muse assesses early traction in non-traditional markets, and breaks down the persistent funding gap facing women founders.
We also discuss:
How AI could transform women’s health
Why traditional VCs struggle to spot these opportunities
What needs to change to solve the “2% problem” in venture capital
Whether you're fundraising or building for an underserved market, this conversation offers tactical insights you can apply right now.
RUNTIME 49:49
EPISODE BREAKDOWN
(1:57) How Rachel connected with Muse Capital Founding Partner Assia Grazioli-Venier
(3:43) Why “care, live and play” are the sectors they’re most interested in
(8:04) “ Entrepreneurs struggle in this space because typically the people that are building are female or diverse — building for their own.”
(11:45) Many investors still don’t recognize that women’s health is a “ massive market opportunity.”
(14:52) What are some of the signals that tell her a founder is ready to work with investors?
(17:06) When it comes to domain expertise, “ our bar is pretty high.”
(19:47) Muse Capital’s process for analyzing market opportunities and evaluating founders
(24:26) How seed-stage founders should prepare for their first VC meeting(27:10) “When a founder comes in and says, ‘nobody's doing what we're doing,’ I'm like, ‘red flag.’”
(29:33) When it comes to women’s health, “ there's really interesting things that can be done with AI around unique data or proprietary data sets.”
(34:44) How is the current political environment impacting innovation/investment in women’s health?
(37:44) Why less than 2% of venture capital goes to startups led by women
(42:52) “ I do think we are going in the right direction. It's just gonna take a lot.”
(44:45) How to get more women into the VC pipeline
(47:45)  If you could snap your fingers today and change one thing about VC, what would it be?
LINKS
Rachel Springate
Assia Grazioli-Venier
Muse Capital
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Thanks for listening!
– Walter.
 

Creative Ops at Startup Speed: Lessons from Superside

Fredrik Thomassen, co-founder and CEO of Superside, joins the show to unpack how startups can scale creative work without slowing down or burning out their teams.
Superside is a subscription-based design company that helps fast-growing teams get high-quality creative at scale. In this conversation, Fredrik shares how he built a globally distributed team, why async collaboration beats real-time meetings, and what most startups get wrong when managing creative work.
We also get into:
Hiring in overlooked markets
Building customer trust and employee cohesion across time zones
Structuring creative operations like a product team
Why treating designers as partners — not vendors — drives better outcomes
If you're juggling growth and messaging or just trying to build creative capacity without the chaos, listen in.
RUNTIME 44:58
EPISODE BREAKDOWN
(2:30) “ You start out and think, ‘I can do this for four or five years,’ and all of a sudden, a decade has passed.”
(4:32) Superside’s beta was popular, but “ it was a total mess behind the scenes.”
(7:36) Why “ it felt like an obvious move to go to YC.”
(11:15) “ We found product-market fit, and then kind of COVID hit at the same time.”
(14:17) The biggest mistake Fredrik made while adding headcount in the early days
(18:59) Working with a founder coach has been “scary, but also in a sense, very motivating.”
(21:39) Fredrik lists his preferred Norwegian authors
(25:29) Inside Superside’s pivot from freelancer marketplace to enterprise creative services
(29:40) “ What's growing at the moment is AI-powered creative services for our enterprise customers.”
(32:08) Quantifying the efficiency gai”s from using AI-enabled services
(37:53) How Superside collaborates with clients to provide strategic services and production work
(40:31) “ It's quite hard to build a lifestyle business.”
(42:40) The one question he’d have to ask the CEO before accepting a job offer with an early-stage startup
LINKS
Fredrik Thomassen
Haakon Heir
Jing Venås Kjeldsen
Superside
Y Combinator
Paul Graham essays
Hunger, Knut Hamsun
Jon Fosse
Karl Ove Knausgård
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Thanks for listening!
– Walter.

How to Pitch VCs Like a “Dangerous” Founder

What makes a founder dangerous?
Not credentials. Not their pedigree. And it's not who they know.
For investor and former operator Promise Phelon, a dangerous founder is someone with lived experience, relentless conviction, and the ability to build something the world doesn't expect.
Promise is the founder and managing partner of Growth Warrior Capital, an early-stage venture firm that invests in founders building seed and Series A enterprise AI companies.
In this episode, she shares hard-won lessons from the founder’s seat and the investor’s table: how to turn capital scarcity into a strategic advantage, navigating the shift from founder to CEO, and why storytelling can’t replace traction.
We also talk about:
How to find the investors who already have reasons to believe
The “puzzle vs. mystery” framework for prioritizing execution
What a dangerous founder pitch actually sounds like
How underrepresented founders can cultivate an appetite for risk — without a safety net
If you're building in stealth, raising without a network, or just wondering how to scale yourself as your company grows, this episode will give you a framework and some momentum.
RUNTIME 59:08
EPISODE BREAKDOWN
(04:32) Promise talks about her path from operator to investor
(06:57) Inside Growth Warrior Capital’’s investment strategy
(09:25) What her typical work week looks like
(14:01) “We love the qualitative, but our goal is to get to the meat of what's going on.”
(16:36) How Promise prefers to be pitched
(18:21) Growth Warrior Capital has plans for a second fund in the works
(21:27) Why more founders need to evolve from being firestarters to fiduciaries
(25:13) Where inexperienced entrepreneurs need the most help
(28:13) “ We look for coachability in a founder. We also look for rigidity.”
(30:50) “ A dangerous founder is someone that you don't expect to come up and kick you in the teeth.”
(34:01) “ …So Kendrick Lamar is the soundtrack for every single investor meeting.”
(36:09) What it’s like to be pitched by a dangerous founder
(39:30) One myth about successful founders that’s holding people back
(44:23) How to cultivate an appetite for risk when you don’t have a safety net
(50:41) What happens when founders learn to make bold strategic moves
(53:09)  ”As a founder, you're not trying to convince anyone of anything. It's a search problem.”
(57:14)  Something Promise used to believe about venture capital that is just totally untrue
LINKS
Promise Phelon
Growth Warrior Capital
Almanack of Naval Ravikant
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Thanks for listening!
– Walter.

The 5-Year Ramp: How Alcatraz Scaled in Enterprise Security

What kind of founder spends five years building a product before going to market?
One who's trying to solve a very hard problem.
Vince Gaydarzhiev is the founder of Alcatraz, a deep tech startup that uses facial authentication. The platform isn’t used to lock people out of single offices or consumer gadgets; its customers are buying global enterprise security, where compliance is strict, trust is earned, and failure isn't an option.
In this episode, Vince shares the emotional, strategic, and technical realities of building a company at the intersection of AI, hardware, and enterprise infrastructure. From working nights on prototypes with a tiny team to navigating founder isolation and breaking into risk-averse markets with no Silicon Valley network, Vince takes us inside the long game of building something real.
We cover:
Why it took three years to get a product into customer hands — and two more to scale it
Validating a deep tech startup when you're not an insider
What enterprise security leaders really care about (and how not to sell to them)
Why founder empathy and “becoming your customer” are non-negotiable in this space
The hiring philosophy that helped Alcatraz scale with high-agency, low-ego team members
How Vince de-risked himself to earn trust from investors and prospective hires
If you're building something technically ambitious or thinking about launching a startup in AI, hardware, or security, listen in.
RUNTIME 32:15
EPISODE BREAKDOWN
(2:35) Where the idea for Alcatraz came from and why Vince decided to take the leap
(5:51) His process for validating the concept with investors, customers, and security teams
(9:37) “I  was surprised that this thing didn't exist yet.”
(11:48) Why it took five years to develop a “globally scalable” minimum viable product
(13:29) How much has his TAM estimate changed since entering the market?
(17:55) The pitch Vince used to recruit employees away from Apple and other top companies
(20:05) “ In 2016, investors were investing into companies purely on a deck.”
(22:18) “ I had zero network. It was my first time.”
(24:42) “ Many people mentally cannot take ‘nos’ in bulk. They get depressed, they feel it's personal.”
(26:50) Why the name “Alcatraz?”
(28:12) “ It's really tough to work with people that you don't like. Very tough. It's never gonna work out.”
(30:24) The one question Vince would have to ask the CEO if he were interviewing at an early-stage startup
LINKS
Vince Gardarzhiev
Alcatraz
Alcatraz AI Raises $6.1M in Funding for Frictionless Access Control, 4/27/2021, press release
Alcatraz AI Receives $25M Series A Funding to Accelerate International Growth, 9/13/2022, press release
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Thanks for listening!
 
– Walter.

From Play to Pay: How Soundtrack Uses PQLs to Drive Growth

What turns a free trial user into a paying customer?
For Ola Sars, founder and CEO of Soundtrack, the answer is all about behavior. In this episode, we break down how his team uses product-led growth (PLG) and product-qualified leads (PQLs) to drive conversions. 
You'll hear how playing 100 tracks became a key signal for purchase intent, the tactics Soundtrack deploys to help self-serve customers experience value fast, and what it takes to scale a SaaS business in a market ruled by consumer giants.
If you're building a PLG motion or trying to convert lookie-loos into cash customers, listen in.
RUNTIME 45:20
EPISODE BREAKDOWN
(3:11) “ It's 20 years now I've been trying to make a living here in the intersection of audio, music and technology.”
(5:22) How Ola became a member of Beats’ founding team.
(9:37) Why he returned to Stockholm to build Soundtrack instead of remaining stateside.
(13:38) When Ola started to learn about product-led growth.
(15:38) “ It's a $40-50 billion market on an annual basis. And we're kind of the only company going after that market right now.”
(18:54) “ We had this approach that everything had to be done self-serve.”
(20:33) Creating a framework to ID and leverage product-qualfied leads (PQLs).
(26:06) What role will AI play in music distribution and production?
(28:23) The gaps Ola sees in today’s music technology marketplace.
(32:04) Why AI-generated music “ doesn't make any sense.”
(35:03) Ola reflects on several cultural shifts that have made it “much easier now” to build in Europe.
(38:12) Stockholm’s entrepreneurs are “kind of hybrid Americans in a way how we think about business.”
(42:08) The biggest myth Americans believe about starting up in Europe.
(44:09) If you were interviewing for a job with an early-stage startup, what’s one question you’d have to ask the CEO before you could accept an offer?
LINKS
Ola Sars
Soundtrack
B2B music streaming service Soundtrack Your Brand raises $15 million, Tech.eu
​​What is “lagom?”, Study in Sweden
The English term "mid" matches the Swedish term "bland, mellan,” tok-pisin.com
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Thanks for listening!
– Walter.

From ML Engineer to CEO: Brightwave's Mike Conover on Turning Technical Vision into Company Strategy

Mike Conover started his career as a machine learning engineer. Today, he’s the co-founder and CEO of Brightwave, an AI startup helping financial professionals make faster decisions with massive, unstructured data.
In this episode of Fund/Build/Scale, Mike shares how he made the leap from technical contributor to strategic leader—and the hard lessons he learned along the way.
From translating technical vision into a focused go-to-market strategy, to learning how to coach, hire, and scale intentionally, Mike unpacks the mindset shift required to move from building code to building a company.
We also get into:
How Brightwave validates new product bets in a high-stakes industry
Why founder-market fit is emotional, not just strategic
Mistakes to avoid when hiring your early team
How to create focus loops and feedback channels before feature creep sets in
Why emotional intelligence and execution velocity matter just as much as AI architecture
If you're a technical founder — or thinking about becoming one — this conversation offers an unvarnished look at what it actually takes to scale yourself while scaling your startup.
RUNTIME 55:09
EPISODE BREAKDOWN
(1:12) Mike explains how Brightwave works.
(3:49) Where the idea came from.
(7:47) How he connected with co-founder Brandon Kotara.
(10:58) The biggest challenges he faced shifting from an engineering role to founder/CEO.
(14:22) “As a CEO, you have to do a lot of jobs that you have no preparation for.”
(15:07) Working with a coach has been “such a sustaining source of inspiration, but also continuity.”
(18:45) “There's a rap lyric I really like, which is, ‘you can't crush me, I'm dirt.’”
(20:29) Turning “reasonable” feature requests into new products helped Brightwave build customer trust.
(25:30) “ It's unusual,” but co-pilots and POC programs were not part of their early success.
(30:12) Tips for building feedback loops between customers and the product team.
(36:04) Seed to Series A “ was about four months.”
(40:02) “ Most startups are not that defensible.”
(45:54) “A lot of the product-led growth techniques that you might use don't always fit the market especially well.”
(47:45) How to create a self-assessment framework for founder-market fit.
(50:43) “ Brightwave — in its full totality — has material substance in my mind already.”
(53:05) The one question he'd have to ask the CEO before taking a startup job.
LINKS
Mike Conover
Brandon Kotara
Brightwave
Fred Kofman, Conscious Business
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Thanks for listening!
– Walter.

What Investors Really Want From AI Founders

Igor Taber has sat on both sides of the table: first as a VC at Intel Capital, then as an operator at high-growth AI startup DataRobot. Now, as co-founder of Cortical Ventures, he’s backing the next generation of AI-first startups.
In this episode, Igor shares how his operating experience reshaped his investment lens, what most VCs still miss about early-stage execution, and how founders can break through the AI noise to build something that actually lasts.
We also get into:
What it really takes to build conviction at the seed stage
How Cortical Ventures defines “defensibility” in AI
The questions every founder should ask an investor (but usually doesn’t)
Why your biggest advantage may not be your model — it’s your momentum
If you’re building in AI, fundraising, or trying to turn early traction into a long-term advantage, download this episode.
RUNTIME: 39:52
EPISODE BREAKDOWN
(1:19) Igor: My investor-operator-investor path was “ a really interesting progression.”
(3:33) Previously, a lot of his opinions were rooted in the “VC echo chamber.”
(6:56) “ You just try to do your best to be a good partner and be helpful.”
(7:43) Why he and co-founder Jeremy Achin started Cortico.
(13:39) What makes an early-stage AI team stand out?
(17:15) When it comes to solo vs. team, “ we haven't seen any like material difference in outcome.”
(18:56) “ I think the biggest company on LinkedIn is called ‘Stealth.’”
(22:17) Why TAM isn’t a major consideration when evaluating new opportunities.
(24:18) His framework for evaluating and validating seed-stage startups.
(26:03) The biggest red flags in founder discovery meetings.
(28:21) Top mistakes founders make in the first year after closing a seed round.
(33:16) How Cortical advises AI founders to build more resilient companies.
(35:55) A few things to keep in mind before quitting a secure job to launch a startup.
(38:07) How to make yourself more investible in 2025.
LINKS
Igor Tabor
Jeremy Achin
Cortical Ventures
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Thanks for listening!
 
– Walter.