An Operator’s Playbook for Monetizing Product-Led Growth
What do you do when everyone loves your product but no one’s paying for it? That was the challenge facing Beautiful.ai. Founder Mitch Grasso nailed the product, but to build a sustainable business, he brought in operator Jason Lapp as CEO.
In this conversation, Jason shares how Beautiful.ai killed its freemium tier, introduced a credit-card-gated trial without losing momentum, and learned to serve both self-serve and enterprise customers at the same time. He also explains how to listen to customer feedback without becoming a feature factory, and why non-technical founders shouldn’t try to know everything about the tech stack.
If you’re a founder wondering when to put up a paywall — or how to balance PLG with enterprise sales — here's a playbook.
RUNTIME 46:20
EPISODE BREAKDOWN
(3:35) “ The timing of us coming together was really fortuitous for beautiful because he had already built the first version of beautiful and put it in market.”
(6:28) “ Microsoft and Google report that there's close to a billion people that use presentation software on a monthly basis.”
(10:51) “ At a certain point after getting in market, you start to get a different set of signal.”
(14:52) The free trial period is a great opportunity to learn about what customers value most.
(19:56) Leverage “emotional” feedback to improve the customer experience.
(23:46) “ We do have a guiding principle, which is: on the customer side, we generally don't build for one customer need.”
(26:17) Beautiful.ai uses NPS surveys to gather feedback from enterprise and individual users.
(28:49) Since pivoting to paid, they have separate teams for enterprise and individual customers.
(23:02) “ We think about an ICP, and then we think about an IECP, meaning the enterprise as a whole.”
(33:57) Capturing behavioral and attitudinal data to understand customer behavior.
(37:18) How the broader rise of generative AI has influenced GTM strategy.
(42:33) Jason shares some advice for non-technical CEOs.
LINKS
Jason Lapp
Beautiful.ai
AI Isn’t Coming For Jobs, It’s Coming For Inefficiency
Continuous Discovery Habits: Discover Products that Create Customer Value and Business Value, Teresa Torres
Everything You Need to Know About Freemium Pricing, Kyle Poyar, OpenView Partners
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Thanks for listening!
– Walter.
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46:20
Building a Bridge Across the Valley of Death
Frontier tech startups don’t fail because the science is bad — they fail because no one needs what they’re building.
In this episode, Roadrunner Venture Studios CEO/co-founder Adam Hammer explains how to avoid that fate.
We talk about why the U.S. struggles to turn research into startups, why being right isn’t enough, and what it really takes to cross the Valley of Death between lab science and real-world demand.
Along the way, Adam shares practical insights for first-time founders, including:
How to test whether your problem is painful enough to sell
What the studio model offers that VCs and accelerators can’t
Why most technical founders struggle with pitching — and how to fix it
And what scientists need to unlearn to become CEOs
If you’re building something deep, hard, or new — don’t skip this one.
RUNTIME 41:11
EPISODE BREAKDOWN
(2:32) How a career spanning national labs, venture capital, and startup leadership led to Roadrunner Venture Studios.
(7:46) “ Our goal is to compress all the mistakes that you would make in a three-year period into a year.”
(8:50) The three frontier tech sectors Roadrunner focuses on: advanced energy, advanced manufacturing, and advanced compute.
(10:28) Why it’s so hard to translate lab science into sustainable, venture-scale businesses.
(13:49) Adam shares ideas for bridging America’s structural gap in commercializing frontier tech.
(16:38) “ Roadrunner serves as a de-risking mechanism for ideas and for people.”
(21:12) “ In science, you win by being right. But in startups, you win by being useful.”
(24:23) What Adam looks for in a pitch deck.
(27:15) When it comes to sourcing founders and ideas, “ we are as early as it gets.”
(31:54) Why Roadrunner Venture Studios set up shop in New Mexico.
(34:16) If he could fix one common founder misconception, what would it be?
(36:26) “ There's nothing innate that predetermines whether somebody can or cannot be a founder.”
LINKS
Adam Hammer
Roadrunner Venture Studios
The Engine
Overcoming the Valley of Death: A New Model for High Technology Startups
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Thanks for listening!
– Walter.
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41:11
Are You *Really* Ready to Raise a Round? Here’s How to Tell
You don’t need a Stanford degree or a flashy deck to raise a pre-seed, seed or Series A, but you do need to show investors that you’ve put in the work.
645 Ventures co-founder Nnamdi Okike shares practical advice for founders who are prepping to raise capital, including what he looks for in pitch meetings, how to uncover “earned secrets,” and why chasing hot categories can backfire.
We also dig into how 645 uses outbound sourcing and proprietary software to spot overlooked talent — and what it really takes to stand out if you don't fit the typical founder mold.
RUNTIME 58:08
EPISODE BREAKDOWN
(2:18) Nnamdi describes his path from operator to investor.
(5:00) Stage by stage: What sets 645 Ventures apart from other firms?
(12:33) What signals and sectors suggest strong alignment with 645?
(21:04) “We do have some solo founders in the portfolio.”
(25:49) His take on CEOs who promote a hard-charging, aggressive culture.
(31:20) Why he favors founders solving real problems, not just chasing trends.
(37:02) One thing he wishes more first-time founders understood about the early-stage ecosystem.
(43:55) What kind of proof or evidence he looks for in companies raising capital.
(49:20) Which early assumptions he and his team have since modified —or thrown out.
LINKS
Nnamdi Okike
Aaron Holiday
645 Ventures
Pattern Breakers
Karen Moon
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Thanks for listening!
– Walter.
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58:08
From Side Project to Series B: How Learning Led to Product-Market Fit
Dan Lee co-founded what would become Nooks while on leave from Stanford. He wasn’t solving sales. He was exploring remote collaboration during the pandemic.
But when they noticed that some of his most active users were in sales development — and that investors were starting to reach out — he followed the signal.
Today, Nooks is a sales AI platform used by teams at Seismic, Fivetran, and Modern Health, with $70 million in funding from Kleiner Perkins, Lachy Groom, and others.
In this episode, we talk about how Nooks evolved from a virtual office for remote collaboration into a fast-growing AI sales assistant platform. Dan shares what it’s like to raise a $43M Series B after an unplanned Series A, why he believes sales needs AI assistants, not agents, and how he built conviction in a space he had no background in.
If you’re an early-stage founder wondering how to navigate a pivot, build for an industry you’ve never worked in, or generate investor pull instead of push, listen in.
RUNTIME 36:32
EPISODE BREAKDOWN
(3:01) “ It started as a project, obviously became a company.”
(5:13) “ Everyone here is smarter than me in some way.”
(5:46) Which early signals indicated Nooks could be more than a side project?
(8:01) “ And then, investors approached and said, ‘oh, you should raise some money.’”
(10:11) “ I think it's a misconception to think that in the early days it's hard to do much without raising money.”
(11:15) Pivoting Nooks from a virtual collaboration platform to serving sales teams.
(14:26) “ At the time, it felt more like a focus than a pivot.”
(16:56) “ Coming from an engineering background, it's easy to think, ‘oh, sales, that's like a dirty job.’”
(20:50) “ We've been fortunate to have a very strong feedback loop with our users.”
(22:20) If you don’t have domain expertise, “ build a mental model of what is true north in terms of product value.”
(23:22) Nooks’ work culture is underpinned by two values: “ask why,” and “earn customer love.”
(26:25) Customer satisfaction ≠ Customer delight
(30:36) Why Nooks is building AI assistants, not AI agents.
(32:41) When it comes to hiring, Dan looks for people with “motivations that align well with Nooks.”
(34:39) One question Dan would have to ask a CEO if he were interviewing for a job with an early-stage startup.
LINKS
Dan Lee
Nooks
Nikhil Cheerla
Rohan Suri
Nooks raises $43M Series B from Kleiner Perkins and launches AI Sales Assistant Platform
Forbes 30 Under 30 AI
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Thanks for listening!
– Walter.
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36:32
Building Hard Tech: Lessons on Funding, Teams, and Timelines
UPDATE: On 9/8/2025, ZEI announced "the conclusion of its operations."
https://www.linkedin.com/posts/zeroei_zero-emission-industries-zei-announces-activity-7371012829409177601-yQph?
*******
Transforming breakthrough research into a sustainable company is never simple — especially in hard tech.
In this episode recorded in December 2024, Zero Emission Industries CEO/founder Dr. Joseph Pratt and Chief Strategy Officer John Motlow share what it takes to move hydrogen power systems from the lab to the marketplace. We talk about raising money in tough conditions, why government grants can be both a blessing and a constraint, and how to build teams that thrive under pressure. Along the way, they offer candid lessons on funding, hiring, and navigating timelines that rarely go as planned.
RUNTIME 51:52
EPISODE BREAKDOWN
(2:11) “ I knew the path on how to solve it and knew that there was demand for it, and took the jump out of the national lab to start the company.”
(6:36) “ I didn't jump into this with a big network of investors.”
(8:57) How ZEI produced the world’s first commercial fuel cell ferry.
(10:56) Why the company’s first hire was a Chief Strategy Officer.
(12:53) John Motlow says he wanted to join ZEI “because it was incredibly risky.”
(17:06) Crafting ZEI’s GTM strategy for the FCV Vanguard, a hydrogen-powered, high-performance speedboat.
(21:55) Is ZEI a transportation company, or a clean tech startup?
(24:20) When it comes to deep tech, customer requirements are wayfinders for PMF.
(29:47) “Government funding and their insights is sort of half the picture.”
(35:30) “ To be clear, we talked to a lot of investors who did not agree with our TAM.”
(39:09) Why they overindexed on hiring employees who have a background in motorsports.
(42:19) Joe’s advice for building specialized teams in a competitive market.
(47:38) “ Don't slot someone in there and then forget about it: Where are their strengths?”
(49:27) What’s next for ZEI?
LINKS
Zero Emission Industries
Dr. Joseph Pratt
John Moslow
FCV Vanguard — Live Demo (YouTube)
ZEI Raises $8.75 Million in Series A Funding
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Thanks for listening!
– Walter.
After working for years in early-stage startups and as a journalist, here are three hard truths I’ve learned:
1. Success in Silicon Valley hinges on connections, hard work and luck.
2. Startups often fail because founders lack fundamental business knowledge.
3. Real, actionable advice comes from those who’ve actually done it.
There’s no such thing as “founder DNA.” If you’re willing to take on risk and invest years of your life in something that has maybe a 10% chance of paying off — less if you’re a woman or person of color — you can be a startup founder.
Here’s why I founded Fund/Build/Scale:
1. To help founders make fewer mistakes.
2. To share successful strategies that can accelerate your go-to-market journey.
3. To inspire more people to see themselves as potential founders. There’s a lot of overlooked talent out there, and we are missing out.
This podcast is for anyone who’s interested in learning the basic skills required to launch a startup, secure initial funding and transform an idea into a sustainable business.
I’m talking to guests about everything: finding a co-founder, conducting customer discovery, recruiting early employees, developing a PLG strategy, fundraising when you’re outside a major tech hub — all of it.
Interested? Subscribe to Fund/Build/Scale on all major platforms and follow the podcast on LinkedIn to get articles, excerpts, transcripts and more.
Fund/Build/Scale is a production of Truth and Soul Media LLC.