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.

(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. 

Chris Barbin

Tercera

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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.

(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? 

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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:

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.

(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.

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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.

(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.

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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:

If you’re building something deep, hard, or new — don’t skip this one.

(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.”

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– 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.

(2:18) Nnamdi describes his path from operator to investor.

(5:00) Stage by stage: What sets 645 Ventures apart from other firms?

(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.

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– 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.

(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.

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Thanks for listening!

– Walter.

UPDATE: On 9/8/2025, ZEI announced "the conclusion of its operations."

*******

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.

(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?

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Rob Biederman has sat on both sides of the table — first as co-founder and CEO of Catalant Technologies, and now as managing partner at Asymmetric Capital Partners. In this candid conversation, he explains why so much of the conventional wisdom around startups is actually counterproductive.

He breaks down why design partners don’t equal traction, why headcount growth is a vanity metric, and why Silicon Valley should stop romanticizing failure. He also shares how Asymmetric evaluates founders, what investors really care about, and the simple test every startup should use to prove they’re solving a real problem.

If you’re a founder chasing milestones that look good on a pitch deck but don’t move the business forward, this episode of Fund/Build/Scale is a reality check you won’t hear anywhere else.

(2:46) “ We have a probably a couple points of differentiation with the broader market.”

(4:46) “ Our happiest spot is kind of in the two-to-six million range for our first check.”

(5:39) “ We want to get to know people probably a year or two before they're going to found so we can really see what they're about and really understand.”

(7:20) “ I think we'd hire most of our founders as investors at our firm, if we had the chance.”

(10:11) What makes a startup  relevant, credible, or just differentiated?

(11:32) An easy framework for self-auditing your startup idea.

(13:09) “ I think our industry kind of worships at the altar of failure a little too much.”

(15:08) “ We don't actually really love backing people directly from really big companies.”

(17:00) Rob explains why design partners are a distraction, not a path to real traction.

(21:23) “ If you're gonna get one career, why not spend it trying to trick the world into doing something differently?”

(24:17) One metric founders love that does not predict success from an investor’s perspective.

(25:08) Inside Asymmetric Capital Partners’ four-step pitch review process.

(27:27) Why the best data rooms are simple: “they have no spin.”

(29:46) Rob describes how his firm’s advisor partner model works.

(31:49) The first step in GTM: “ get to the bottom of why your customer is buying from you.”

(35:18) At the start, tell investors “everything you haven't figured out” so you can start planning.

(38:17) “ If you don't tell your doctor the truth, what can they do for you?”

(41:02) What he would do differently if he were launching a startup today.

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Thanks for listening!

– Walter.

Pro tip: If you can’t see yourself getting up every morning for the next ten years and being excited about going to work, don’t launch a startup.

Ajay Prakash co-founded Rinse in 2013 to take the friction out of laundry and dry cleaning — for consumers, and for the small, family-owned businesses behind the counter.

Since then, Rinse has scaled into a national brand, and Ajay has become a lecturer at Stanford Graduate Business School’s Startup Garage, where he teaches frameworks for validating ideas, testing business models, and knowing when it’s time to take the leap into entrepreneurship.

I invited him on to share what he’s learned about developing domain expertise from scratch, building trust with co-founders, and avoiding the early mistakes that can derail a promising business.

(2:22) Ajay talks about two trends that led him to co-found Rinse in 2013.

(4:15) Rinse co-founder James Joun was “one of my best friends from college.”

(5:29) “When we started, we spent a lot of time with James’ parents in the dry-cleaning store.”

(6:40) Before taking the leap, founders should identify their “passion, expertise, and market opportunity.”

(9:11) “As you build a company, answering the question of ‘why now’ and ‘why me’ is really important.”

(11:19) “We signed up 11 of our friends. We picked up their clothes.”

(14:17) “Every smart investor we talked to… told us we had to be on-demand.”

(17:41) Early signals led Rinse to pivot from pricing per pound to adopting a subscription model.

(20:23) His approach to crafting customer personas.

(22:05) “We always envisioned helping the local cleaners.”

(27:11) From the start, Rinse used Net Promoter Scores and surveys to glean customer insights.

(30:44) The “two general areas of lessons” Ajay teaches at Stanford’s Startup Garage.

(34:53) Why he encourages Startup Garage students to keep asking themselves, “Am I still excited?”

(37:41) How to prepare for the mental challenges of being a startup founder.

(40:01) Is Rinse’s operational model adaptable to other industries and services?

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Thanks for listening!

– Walter.