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 SUBSCRIBE   📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   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 SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/ 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 SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   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 SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   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 SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   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 SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   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 SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   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 SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening!   – Walter.

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/   📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   Thanks for listening! – Walter.

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.   RUNTIME 43:43   EPISODE BREAKDOWN (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. LINKS Rob Biederman Asymmetric Capital Partners Asymmetric FAQs Catalant Technologies Democratizing Care: Announcing our Investment in Counsel Health EvolutionIQ Raises $21M Series A To Deliver AI Based Claims Guidance Across The Industry SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   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. RUNTIME 42:38 EPISODE BREAKDOWN (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? LINKS Ajay Prakash James Joun Rinse The Four Steps to the Epiphany, Steven G. Blank The Lean Startup, Eric Ries Startup Garage at Stanford Graduate School of Business SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening! – Walter.

Karthee Madasamy is the founder of VC firm MFV Partners and the founding managing partner of Harper Court Ventures, both of which focus on early-stage deep tech startups. In this episode of Fund/Build/Scale, he explains what early-stage founders get wrong about TAM, why technical validation isn’t enough, and how to de-risk your company when the market barely exists. We also talk about: What MFV looks for when evaluating scientific founders The importance of “market inevitability” and strategic timing Common missteps deep tech founders make on the road to Series A If you’re building ambitious technology in a complex, slow-moving market, this episode will help you speak investors’ language — and build a company they can believe in.   RUNTIME 41:03   EPISODE BREAKDOWN (2:24) Karthee describes his engineer–product manager–VC career path.(4:37) How does MFV Partners define deep tech?(6:35) Areas of interest include robotics, physical AI, and next-gen computing—“especially quantum.”(8:39) “We are doing anywhere from pre-seed to seed, up to all the way to Series A.”(12:17) About a third of the founders he works with are transitioning from academic or research roles.(14:01) Inside MFV’s due diligence process.(16:20) The three questions Karthee uses to frame his first meeting with a founder.(17:47) Tactics for engineers and academics who want to validate their idea but lack customer experience.(19:27) “There's no fallback. You have to basically go deep on one thing.”(23:43) “A deep tech founder, in addition to all the other risks, they're taking technical risks.”(25:51) What does traction look like at an early-stage deep tech startup?(28:38) Be prepared to answer this question during your first meeting with Karthee.(30:32) “In deep tech, oftentimes, there is not a place you can just go to get a TAM.”(37:40) Why MFV accepts cold pitches.(39:24) The one question Karthee would ask the CEO if he were interviewing for a job at an early-stage startup. LINKS Karthee Madasamy MFV Partners Harper Court Ventures SUBSCRIBE 📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   Thanks for listening!   – Walter.

Jyoti Bansal sold his first company, AppDynamics, to Cisco for $3.7 billion. Harness, his next company, reached a similar valuation a few years later. As an entrepreneur — and as a VC at Unusual Ventures — Jyoti has built and backed multiple billion-dollar startups. But despite his track record, he says technical founders often overlook the same hard truth: good ideas don’t build great companies. It’s all about execution. In this conversation, Jyoti explains how he helps engineers become CEOs, the leadership frameworks he uses to scale fast without breaking culture, and why each business unit inside Harness runs like a startup of its own. He also talks about what he had to unlearn as he made the leap from founder to investor, and debunks the myth that every entrepreneur needs a mentor. If you’re aiming for breakout scale, this episode will give you some useful tactics — and maybe a few reality checks. RUNTIME 44:24 EPISODE BREAKDOWN (3:23) “ I started Big Labs and I call it a startup studio: it's really my lab, a research lab for me to experiment with ideas and projects that I'm excited about.” (6:15) Why Jyoti still carves out time for customer discovery and sales calls.(7:27) “ Harness is designed for kind of this next-generation, AI-based approach for DevOps.”(9:42) “ Our entire philosophy is built with this concept called ‘startups within a startup.’”(11:22) How Harness maintains cohesion and alignment across 16 different modules.(14:00) The specific traits and abilities Jyoti looks for when hiring leaders at Harness.(17:35) Why some engineers are poorly suited to make the leap into entrepreneurship.(20:55) A mental framework that helped Jyoti become a better manager and communicator.(23:59) “ I always leaned on topic-based mentorship, not generic mentorship, which is a particular problem.”(25:53) Why working with a CEO coach “didn’t work very well for me.”(27:36) The sectors and types of startups that interest him the most right now.(30:10) How he prefers to be pitched — and how to apply to Unusual Academy’s next cohort.(32:24) “ 30, 40% growth rates are where most startups should be looking, at least — ideally much more.”(33:53) “ If we can't see a path to $100M of revenue — or a billion of revenue — we don't invest.”(37:15) The biggest attachment he had to let go of when transitioning from founder to VC.(42:41) The one question he’d ask the CEO if he were interviewing for a job with an early-stage startup. LINKS Jyoti Bansal Harness Traceable Unusual Ventures Unusual Academy Unusual Field Guide Cisco Announces Intent to Acquire Application Performance Monitoring Leader AppDynamics, 1/24/2017 SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/ Thanks for listening! – Walter.

Brian Rothenberg, partner at Defy and former VP of Growth at Eventbrite, joins Fund/Build/Scale to share what really matters when evaluating early-stage startups. From spotting false signals of traction to building defensible business models, Brian offers practical advice for both founders and operators. He also explains why job seekers should “think like a VC” before joining a startup, how he prefers to be pitched, and what signals he looks for in AI and emerging tech companies. Whether you’re raising capital, building a company, or considering your next role, this conversation will help you see the startup landscape through an investor’s eyes. RUNTIME 34:28   EPISODE BREAKDOWN (2:14) “ I've been fortunate to always be pretty entrepreneurial… it was just how I was wired.” (5:11) How advising friends and investing in their companies led Brian into VC. (6:45) “ The bulk of our capital goes to seed, seed plus or Series A. But we do go as early as an idea and a person.” (7:48) Defy’s areas of interest and average check size. (8:53) “ We will be entering into a period where we'll see a lot of new and profoundly different consumer AI experiences.” (10:26) “ I see a lot of promise in rewiring a lot of the financial infrastructure and plumbing through use of blockchain.” (12:42) The traits and metrics Defy looks for in early-stage AI startups. (14:33) Brian loves Sean Ellis’ customer satisfaction survey. (15:55)  Why proof-of-concept programs don’t generate recurring revenue or reduce churn rates. (19:01) Have you noticed that we don’t hear about many AI startups making a pivot? (21:00) Thanks to AI tools, “ we will see a lot more niche businesses and founders not having to dilute themselves as much as they had previously.” (22:22) How Brian grades the VC community’s ability to judge AI traction. (24:42) Technology alone doesn’t build a defensible startup. (26:57) How to pitch the team at Defy. (29:40) Why startup job seekers need to start thinking like investors. (32:58) The one question Brian would ask the CEO if he were interviewing for a job with an early-stage startup. LINKS Brian Rothenberg Defy Growth with Sean Ellis SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening! – Walter.  

When you’re raising your first rounds, every cap table decision can echo for years. Give away too much equity early, lock yourself into restrictive pro rata rights, or over-optimize for valuation — and you may find yourself boxed in just when your company starts to grow. Pulley co-founder and CEO Yin Wu has seen these mistakes firsthand. In this episode of Fund/Build/Scale, she offers practical, founder-first strategies for structuring and managing your cap table so you can attract top talent, keep your options open, and stay in control of your startup’s destiny. We also discuss how to compete with entrenched incumbents, why her LinkedIn profile says she works in Customer Success, and how founders can shift their role as the company scales. RUNTIME 38:44 EPISODE BREAKDOWN (2:46) Why her LinkedIn profile says she’s in “customer success,” not CEO/co-founder. (5:43)  How much time passed between Day Zero and serving Pulley’s first customer? (9:48) “ You're trying to market the product, and then you're also playing the role of customer success at the same time.” (10:04) The number-one cap table mistake founders make? “Being too greedy.” (13:55) Why are startups sticking with four-year vesting schedules when it takes 7-10 years to exit? (15:14) How founders should think about pro rata rights in early rounds. (19:04) Taking money out in a secondary “ actually releases some of the pressure and allows founders to focus.” (21:04) Founder-preferred shares “are becoming increasingly popular.” (24:15) CEO/founders need to remember “ the soft power that you have as a leader of the company.” (26:45) How Yin defines “founder mode.” (30:50) “ Every successful company has been a response to some incumbent’s worldview.” (33:38) Why going public “ can actually make it tough for companies to be able to innovate.” (34:04) The one question she’d ask the CEO if she were interviewing for a job with an early-stage startup. LINKS Yin Wu Pulley How to Scale a Startup in Just 3 Months, Pulley Employee Equity, Sam Altman Will the Blockbuster Deal for Wiz Spur an M&A Wave in Cybersecurity?, WSJ Pro VC SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn. https://www.linkedin.com/newsletters/7249143254363856897/ 📸 Follow Fund/Build/Scale on Instagram. https://www.instagram.com/fundbuildscale/   Thanks for listening! – Walter.

A turbulent flight sparked Wayne Slavin’s idea for Sure: let consumers buy insurance in real time. But after launching as a D2C app, he realized the bigger opportunity was powering insurance sales for others. Sure’s pivot to B2B turned it into a vertical SaaS platform that lets enterprise companies embed insurance at the point of transaction. In this episode, Wayne explains how to pivot without losing your mission, why founders should lead early enterprise sales, and why he refuses to run proof-of-concept deals. He also shares why — if he could do it over — he’d avoid launching a business with so much built-in complexity. RUNTIME 51:58 EPISODE BREAKDOWN (3:16) How a turbulent flight inspired Wayne to sell insurance directly to consumers. (7:03) Why he reached out to a founder who tried (and failed) to launch an insuretech startup. (12:01) Becoming fluent in insurance industry jargon “was definitely a learning curve.” (16:05) The point when Wayne realized Sure needed to pivot. (20:16) The transition from D2C to B2B “was a slow aircraft carrier style turn.” (22:35) How to tell whether you’re grinding through a rough patch or building on the wrong model. (29:21) When it was time to pitch to enterprise customers, “ most of those conversations were led by me. (32:40) “ Proofs of concept are actually the way for a big company to not do something.” (40:45) Sure is an embedded finance company, not an insurance company. (44:04) “ In hindsight, I would not want to be in another business where you are dependent on two other parties performing.” (49:08) The one question Wayne would have to ask the CEO if he were interviewing for a role with an early-stage startup. LINKS Wayne Slavin Sure "The Start-up From Hell," Inc.com SUBSCRIBE 📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📸 Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening!   – Walter.

James Joaquin is co-founder and managing partner at Obvious Ventures, a VC firm that backs startups tackling intractable problems like climate change, chronic disease, and income inequality.  Their portfolio includes businesses that once sounded like science fiction but are reshaping billion-dollar industries. He says he's looking for technology that will “move humanity forward." But this episode isn’t just about mission-driven investing.  James gets extremely tactical: he breaks down how Obvious evaluates founding teams, how he prefers to be pitched, and how your answer to “why are you building this?” can make or break your shot at getting funded. He also shares a framework for balancing ego with humility, why startups die of indigestion — not starvation — and how his experience building one of Apple’s most famous failures helped him identify category-defining companies. By the end of this conversation, you’ll have a clearer understanding of what top-tier VCs are looking for—and whether your startup has what it takes to earn a “yes.” RUNTIME 46:38 EPISODE BREAKDOWN (2:37) James unpacks the firm’s origin story: “We love to say that all great ideas are obvious in hindsight.” (7:43) What “world-positive” investing looks like in practice. (10:41) When it comes to a founder’s domain expertise, “I  don't think that there's one single archetype.” (13:46)  What's something you used to believe as a founder that changed dramatically after you became an investor?  (15:15) “A lot of the work that I do at Obvious is trying to sniff through the veneer and the BS to get to that authenticity.” (18:13) The most successful founders he’s bet on “were weird, and they were ridiculed by whatever industry they were in at the start.” (19:40) Tactical lessons he learned while working at Apple for six years after they acquired his startup. (23:29) Why generative science has “ become a key investment thesis” for Obvious. (26:48) James is looking for startups that will “ output or generate new scientific breakthroughs.” (29:42) “ You almost cannot think too large in terms of the scale that we're going after.” (33:03) James shares the framework Obvious used to evaluate geothermal startup Zanskar. (37:58) The firm’s sweet spot: startups that are “just one step away from commercialization.” (42:31) “ We don't get lost in the noise of what's going to happen in the next three and a half years.“ (43:54) What kind of startup would he launch today if he wanted to change the world? LINKS James Joaquin Obvious Ventures Biz Stone Beyond Diamond Foundry Virta Health Zanskar Geothermal & Minerals Gusto Xoom What is a B Corp? (B Lab) SUBSCRIBE Get the newsletter Follow Fund/Build/Scale on Instagram Thanks for listening! – Walter.

Uncork Capital Partner Amy Saper shares practical advice for early-stage founders building AI-enabled tools for engineering, product, and design teams, or as she describes them, "products that make you not want to quit your job." Drawing on her experience in product marketing at Twitter, Uber, and Stripe, she explains why storytelling is an underrated founder skill, how to refine your ideal customer profile, and why it’s good to reverse-engineer a roadmap from your Series A goals. She also shares tips for assessing founder/investor fit, when (and when not) to launch, and why she cares more about your conviction than your TAM slide. If you're a technical founder looking to pitch smarter, launch better, and scale leaner, this episode is for you. RUNTIME 40:46 EPISODE BREAKDOWN (3:46) How Amy’s product marketing background informs her investor perspective (8:45) Storytelling skill (and coachability) “ separates the mediocre founders from the exceptional ones.” (12:02) “ I do tend to gravitate towards very technical teams. Sometimes they're all engineers.” (15:16) A few questions Amy would ask a VC if she were an early-stage founder (17:25) How she defines founder conviction — and the traits she looks for (22:56) Identify your goals and targets, then work backwards from there (26:55) “ I have a funny but also kind of real sub-thesis, which is products that make you not want to quit your job.” (28:50) Thanks to new AI tools, “ we're seeing the rise of small lean teams that are achieving early profitability.” (33:45) “ I am a sucker for a great deck or a beautiful presentation.” (36:30) “ I care less about the overall TAM than how you're defining what's addressable.“ (39:27) The one question Amy would have to ask the CEO if she were interviewing for a job with an early-stage startup LINKS Amy Saper Uncork Capital SUBSCRIBE 📓 Get the Fund/Build/Scale newsletter on LinkedIn:  https://www.linkedin.com/newsletters/7249143254363856897/ 📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening! – Walter.

Ten Eleven Ventures CTO and Operating Partner Scott Lundgren shares practical advice for early-stage cybersecurity founders. He explains why founder-market fit matters more than product polish, how teams should think about TAM in fragmented markets, and the signals he looks for in technical pitches. He also breaks down how Ten Eleven’s network helps with diligence and customer development — and why “cool tech” often misses the mark. Plus: his take on the AI hype cycle, and why building credibility starts with listening, not pitching. RUNTIME 38:06 EPISODE BREAKDOWN (3:37) How founding an ISP as a teenager led Scott to a career in tech. (6:06) Why he decided to join Ten Eleven Ventures as CTO/operating partner. (9:53) Scott breaks down the essential elements of a cybersecurity pitch. (14:31) Inexperienced founders, “as a general rule, have no idea about the TAM.”  (17:21) On AI hype: “ I'd like to see some more rigor with how we feel like we can start to quantify some of the benefits.” (20:20) Having a global network of security professionals is “ a really great resource for us as a firm, but also for our founders.” (21:51) Lessons learned from being on Carbon Black’s founding team. (23:59) “ You need both of these things that are intertwined: the luck, and the the hard work.” (26:08) Do customer discovery face-to-face, not over Zoom. “It isn't always productive, but there's no substitute for it.” (30:57) Developing and promoting a startup mindset outside of Silicon Valley. (35:30) “ If you build really cool tech to solve a pretty simple problem, then that probably was over-engineered.” (36:11) How to build investor and future customer relationships — when you still have a job. LINKS Scott Lundgren Ten Eleven Ventures Carbon Black SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening! – Walter.

Construction workers spend hours on their hands and knees snapping chalk lines to mark where walls, plumbing and utilities should go. It’s painstaking, back-breaking labor. And that’s how it’s been done for centuries. Tessa Lau saw an opportunity — and built a robot that does it faster, safer, and with surgical precision. In this episode of Fund/Build/Scale, the Dusty Robotics founder and CEO shares some of what she's learned about transitioning from a researcher to a deep tech founder, including: How she turned past startup mistakes into a rigorous customer discovery process The structured approach Dusty used to land its first paying customer Why she says stealth mode is overrated — and how building in public gave them a head start How “cool tech” can lead you astray if you’re not solving a real problem Smart ways to pivot and iterate based on actual user feedback What it takes to build a mission-driven team that scales with you If you’re interested in robotics, deep tech, or why some concepts fall into the valley of death while others sail over it like a Red Bull stunt team — listen in. RUNTIME 43:10 EPISODE BREAKDOWN (3:00) “ I always thought I would be a professor someday, and that was my planned career path.” (5:39) How a home renovation project led Tessa into making construction robots (9:16) “ We thought we were going to build a vacuum cleaning robot.” (12:24) “You have to establish that someone is willing to pay for the technology and that it's doable.” (14:15) “ We needed to build something that was 10x better than the status quo in order to scale at venture speed.” (15:41) Finding a deep tech TAM is “ a hard problem, especially when you're creating a new category.” (19:16) “ You can't try to be everything for everyone.” (21:00) Their first prototype “could barely do anything,” but fast pilots helped them iterate quickly. (26:08) How Tessa figured out their pricing *before* they went to market (29:24)  Why marketing and branding are table stakes for a deep-tech startup (33:11) “ As the CEO, you are the face of the company whether you like it or not.” (37:06) “ Our marketing team doesn't need to be very technically savvy.” (38:22) “ I have yet to see a good reason to be in stealth, ever.” (40:53) The one question she’d have to ask a deep tech CEO before accepting a job offer LINKS Tessa Lau Dusty Robotics Philipp Herget, CTO IBM Research Willow Garage, Wikipedia “Savioke is now Relay Robotics,” 5/2/2022, The Robot Report Crossing the Chasm, 3rd edition, Harper Books SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📸 Follow FBS on Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening! – Walter.