Fund/Build/Scale

Recorded live in San Francisco during TechCrunch Disrupt 2025 week, this Fund/Build/Scale session brings together Cyan Banister (Long Journey Ventures) and Cristian Cibils Bernardes (Autograph) for a practical look at building consumer AI and the investor-founder dynamics that make it work. We dig into pre-traction signals that actually predict momentum, how to validate a weird idea, raise smart money, and ship products people return to. Cristian shares Autograph’s first moment of value, retention indicators, and a trust-by-design stance; Cyan unpacks the decision rules and behaviors that earn a second meeting. Together, they outline small-budget experiments and the frameworks they use to create products that stick. For first-time founders and early operators, this episode delivers concrete steps you can start taking tomorrow.
Thanks very much to Jenna Birch and the team at SISU for co-hosting and making this live recording possible!
EPISODE BREAKDOWN
(1:54) Why Cristian named Autograph’s AI agent “Walter.”
(3:37) When they connected, Cristian saw “a bunch of synchronicities along the way that just kept pointing in this direction.”
(4:59) Cyan: “When he showed up and we were sitting together having coffee, I immediately was like, ‘yes.’”
(6:03) The sheer number of coincidences linking these two is unsettling — “quantum entanglement” comes to mind.
(8:18) Cristian and Cyan share their non-consensus takes on consumer AI.
(10:53) Cyan describes the framework she’s using to assess early signals as an investor.
(12:51) “I will not look at your résumé. I won’t look at what you did. Whatever you tell me in that interview is what I’m going to go off of.”
(14:42) “Fundraising is grueling. It was 50 conversations before I met Cyan, and then I had, I think, another 30.”
(16:53) Cyan’s framework for backing vs. passing.
(18:26) The three essential ingredients Long Journey Ventures seeks in founders.
(22:00) What a “magically weird” founder looks like — and why they’re so valuable.
(26:15) A red flag that ensures you won’t get a second meeting with Cyan.
(27:52) A behavior that virtually guarantees a second meeting.
(29:45) Cristian describes Autograph’s moat.
(34:40) “This whole thing doesn’t work if the trust element isn’t there.”
(38:08) What founder-investor fit looks like in their working relationship.
(41:57) One experiment founders should run this week.
(43:10) The most underrated founder superpower.
(44:10) “If you were interviewing for a job at an early-stage startup, what’s one question you’d have to ask the CEO before you could take the offer?”
RUNTIME 47:19
LINKS
Cristian Cibils Bernardes
Cyan Banister
Autograph
Long Journey Ventures
The Ugly Duckling
SISU
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Thanks for listening!
 
– Walter.
***********************************
This event and recording are independently produced by Fund/Build/Scale and co-hosted with SISU. We are not affiliated with, endorsed by, or sponsored by TechCrunch or TechCrunch Disrupt. “TechCrunch” and “Disrupt” are trademarks of their respective owners.

I interviewed Ryan Wang, co-founder and CEO of Assembled, in his San Francisco office to unpack how he turned lessons from Stripe into a fast-growing startup that powers customer support teams at Robinhood, Canva, and Notion.
We talk about:
Finding the right co-founders and surviving a CEO hand-off
Discovering product-market fit by asking one powerful question
Turning a “sleepy” support category into a $200 billion opportunity
Launching a second product with a startup-within-a-startup mindset
What it takes to lead through AI disruption and build for adaptability
Whether you’re building your first team or figuring out your second act, Ryan’s story is a masterclass in scaling deliberately while staying flexible.
RUNTIME 53:40
_
EPISODE BREAKDOWN
(2:35) “ I was employee number 80 or so at Stripe, working on machine learning for fraud detection.”
(5:08) If you’re doing diligent customer discovery, working harder does not get you ahead faster.
(7:27) How Assembled’s founding team, er, assembled.
(8:47) “ There was a period, maybe the first year and a half or so, where there was no CEO.”
(10:33) Ryan explains the mindset that took him from software engineer to CEO.
(12:30) “ ‘Brother mode’ is both a feature and a bug at the same time.”
(14:58) How Assembled arrived at workforce management as its unique value proposition.
(17:48) Ryan talked to more than 100 prospects during the customer discovery process.
(19:00) The exercise they used to develop their initial customer personas.
(22:24) “ We took a really, really long time to hire for product. It was probably four or five years into the company.”
(25:00) Who was Assembled’s first design hire?
(27:26) To acquire product-market fit, “ we started with just a simple automation value proposition.”
(30:26) “ A lot of folks wanted to invest in Stripe alums, and Stripe led our seed.”
(33:35) Why customer support ops is — and will continue to be — such a huge opportunity.
(36:41) A good mission statement defines the change you want to see in the world.
(41:41) “ People who really do feel committed to a large mission, they understand that to get there is gonna require a lot of schlep.”
(43:55) How Assembled used a startup-within-a-startup mindset to innovate.
(48:47) “ We reassigned folks internally, and the key really was the order of operations.”
(51:31) If you were interviewing for a job with an early-stage startup, what’s one question the CEO would have to answer before you could take the offer?
LINKS
Assembled
Ryan Wang
Brian Sze
John Wang
Stripe
Kelly Sims, Thrive Capital
Jack Altman, Alt Capital
Jen Ong Vaughan, Head of Strategic Ops, Stripe
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Thanks for listening!
 
– Walter.
 

When startups fail to scale, it’s rarely because of bad code or bad luck. More likely, it's because they didn’t hire the right people at the right time.
Chris Barbin, founder and CEO of Tercera, shares a playbook for assembling your “Starting Five” — the essential leadership roles every professional services startup needs to grow from $10M to $100M and beyond.
Drawing from decades as an operator and investor, he explains how to spot founder-market fit, when to swap out co-founders, and why hiring someone with a flashy resume can set you back two years.
If you’re building a people-first business, this episode is your blueprint for doing it right the first time.
RUNTIME 35:14
 
EPISODE BREAKDOWN
(2:24) Chris explains how his career path led him to become CEO of Tercera.
(6:18) The most common problems and challenges he helps founders navigate.
(9:17) What stage are the professional services startups Chris typically meets with?
(11:06) How he defines founder-market fit.
(13:31) Red flags that indicate a founder isn’t ready to work with investors.
(16:15) One of the constructs of our fund is [that] none of our investments compete with each other.”
(17:34) After the CEO, “ those five supporting cast members — key lieutenants — are essential.”
(19:11) In most cases, three of the original Starting Five need to be replaced.
(22:29) “ I've fallen into that trap myself — I hired a bunch of those that look amazing on paper.”
(24:29) A framework for finding your first executive marketing hire.
(27:17) Don’t let your board pressure you into making rushed staffing decisions.
(29:37) Managing the ripple effects associated with rebuilding the Starting Five “is really, really hard to do.”
(31:29) Chris shares his preferred format for board meetings.
(33:00) The one thing he wishes every founder understood before they started raising money. 
LINKS
Chris Barbin
Tercera
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Thanks for listening!
 

I’ve explored different aspects of product-market fit on the podcast, but when you’re scaling an open-source business with enterprise customers and a global developer community, you also need customer–engineering fit — the ability to translate between what’s being built and what the market actually needs.
At Astronomer, Viraj Parekh is that bridge. He is part engineer, part strategist, and part customer advocate, working across product, sales, and engineering.
In this episode of Fund/Build/Scale, Viraj explains what a Field CTO really does, how the role evolved at Astronomer, and when founders should consider creating one. He also shares lessons on customer discovery, team dynamics, and how to turn technical insight into business momentum.
RUNTIME 31:16
EPISODE BREAKDOWN
(2:20) What is Astronomer, and when did the company get started?
(3:51) How the founding team came together.
(6:39) How Viraj collaborated with CTO Julian LaNeve to develop the Field CTO role.
(8:28) Where their roles overlap — and where they each take ownership.
(11:42) “We were at a point where we were really trying to standardize our sales process.”
(13:20) How the Field CTO role is different from a sales engineer or solutions architect.
(15:39) “ Talking to customers is a very humbling thing every day because you just realize how much you have to learn.”
(19:14) “ At a really early stage of customer development, the Field CTO role is almost like an external-facing product manager.”
(21:46) Viraj talks about the processes and tools he uses to share customer feedback internally.
(24:48) How to be a staunch customer advocate without losing your business focus.
(26:55) What’s the biggest opportunity cost associated with not having a Field CTO?
(30:13)  If you were interviewing for a job with an early stage startup, what's one question the CEO would have to answer before you could take the offer? 
LINKS
Viraj Parekh
Julian LaNeve
Astronomer
Apache Airflow
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Thanks for listening!
– Walter.

More startups die from co-founder breakups than from running out of money.
Attorney David Siegel, a partner at Grellas Shah LLP, has spent years inside these conflicts, helping founders navigate everything from equity disputes to emotional meltdowns.
In this conversation, he explains:
Why greed and mismatched expectations trigger so many founder breakups
How minority founders can protect themselves before they’re pushed out
What departing founders can realistically expect to walk away with
Why VCs hate “dead weight” on the cap table
The emotional toll of disputes — and why lawyers often play part therapist
If you’re thinking about starting a company with someone else, or already rowing in that two-person boat, this episode will show you what’s at stake — and what to do before it’s too late.
If you thought The Social Network had a happy ending, you might want to skip this one.
RUNTIME 47:35
EPISODE BREAKDOWN
(2:15) Disclaimer: “If you're looking for legal advice, that's something to talk to your own lawyer about.”
(4:14) When it comes to equity distribution, “the fifty-fifties are a 5%.”
(7:14) What are the most common triggers that lead to co-founder breakups?
(11:35) What steps can a minority co-founder take to protect their equity in the earliest stages?
(15:23) Ultimately, “the only person the lead investor knows is the majority founder.”
(17:06) As long as you document all oral agreements, “you should be in good shape.”
(20:04) Draw up agreements for any advisors or consultants you add to the cap table.
(22:36) “The initial calls around a co-founder dispute, we play 50% lawyer, 50% therapist.”
(25:17) “Breakups where it's not a surprise to the founder being kicked out are usually the smoothest.”
(28:05) Once outside money comes in, minority co-founders leave with less than they agreed to.
(30:09) How negotiable is retaining the co-founder title after a breakup?
(32:32) Pre-agreed severance and other ideas for reducing financial pain and hard feelings.
(35:05) “What a minority founder can do: you need face time with the investor.”
(38:44) When should the founder with less equity contact a lawyer?
(41:15) The most common mistakes founders make during a breakup.
(44:43) The one thing David wishes more founders understood before picking a co-founder or investor.
LINKS
David Siegel
Grellas Shah LLP
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Thanks for listening!
– Walter.

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.

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.

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.

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.

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
SUBSCRIBE📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/
 
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Thanks for listening!
– Walter.