Fund/Build/Scale

Startups are built on grit, vision, and — surprisingly — a lot of peer advice. In this episode, I sat down with Mallory Contois, Head of Community at Mercury and leader of Mercury Raise, their founder success platform. Drawing from their latest survey, Mallory shares eye-opening insights about how early-stage entrepreneurs navigate challenges like fundraising, hiring, and customer acquisition. Why do founders rely more on peer networks and podcasts like this one than their VCs for operational advice? Mallory explains the unique psychology that makes it hard for founders to admit uncertainty to their investors and why angel investors often provide more operational value than institutional funds. We also discuss key survey findings, including the evolving AI landscape, the benefits of accelerators, and how lean teams are reshaping what’s possible in a startup.  Whether you’re building your first company or gearing up for the next funding round, this episode offers actionable insights and a fresh take on founder dynamics in today’s startup ecosystem. Subscribe now to Fund/Build/Scale and learn how to turn your idea into a sustainable business. RUNTIME: 44:44 EPISODE BREAKDOWN (2:19) A brief overview of Mercury and Mercury Raise. (3:42) Mallory describes a day in the life of Mercury’s Community team. (6:18) Do mature startups worry about the same things as seed-stage teams? (8:41) “ We have a pretty good pulse on what people are talking about and what people are struggling with.” (9:26) Nearly a quarter of all survey respondents applied to accelerators but were rejected. (11:05) Why founders are more likely to get advice from this podcast than their VCs. (13:39) “ The peer connection that founders have is almost trauma bonding.” (15:02) “ We're seeing founders and investors giving the advice to be much more constrained in spend management.” (17:43) Mallory describes different founder archetypes who are attracted to Mercury Raise. (21:07) “ AI investments now are a lot more calculated than they were in the last couple of years.” (24:45) For AI founders, building in a hype cycle “ can be simultaneously demoralizing and exciting.” (27:17) How Mercury Raise creates value through community. (29:54) Mercury’s Investor Connect program helps founders sharpen pitches. (32:54) “Fundraising in general is just a black box.” (36:13) Vibe check: “solo founders are actually becoming a little bit more common and a little bit more accepted.” (37:19)  ”Co-founder breakups — it's worse than the real thing.” (38:02) Mallory’s advice for founders who are planning to fundraise in 2025. LINKS Mallory Contois Mercury Mercury Raise Mercury Investor Connect SUBSCRIBE 📓Substack: https://fundbuildscale.substack.com 📸 Instagram: https://www.instagram.com/fundbuildscale/ 📥 LinkedIn:https://www.linkedin.com/newsletters/7249143254363856897/ Thanks for listening! – Walter.

In October 2024, New York-based Swell VC announced its second fund with $11.5 million in commitments.  Co-founded by general partners Jay Patil and Rusty Ralston in 2011, the firm now manages two seed-stage funds and a special purpose vehicle with $19 million in assets. Compared to larger firms, they’re small potatoes — but that’s intentional. Swell VC is all about being hands-on: helping founders with critical early hires and go-to-market strategies. I invited them on Fund/Build/Scale to discuss their investment thesis, why diversity matters for building innovative teams, and how to know when it’s finally time to stop thinking about your startup idea and start building. RUNTIME 42:09 EPISODE BREAKDOWN (1:36) Rusty explains how he and Jay met. (4:08) “ People determine the outcome of a company.” (5:36) “ You start the search when you're ready to hire. And then you build momentum.” (8:27) When Swell VC gets involved with founders, where they’re looking to invest. (11:24) Jay talks about the firm’s portfolio strategy and its second fund. (14:38) When it comes to early hiring, “ over the last 15 years, we've codified like all of our learnings.” (17:16) Where do  founders make the most mistakes in the hiring/interview process?  (21:43) “A  big blind spot is thinking diversity is just about hitting certain metrics.” (23:15) “ We're all about finding founders to live on what we call ‘the edge of the inside.’” (26:39) “ No solo founder can do everything forever.” (29:14) “ You don't need to build a full team right away. Your network is kind of your first line.” (31:55) Signals that indicate a founder’s ready to take the leap into entrepreneurship. (34:40) Why Swell VC is looking for category-creating startups to invest in. (37:34) Questions Jay and Rusty expect founders to ask during the discovery meeting. (40:25) How they prefer to be pitched. LINKS Jay Patil Rusty Ralston Swell VC info@swell.vc Swell VC Closes $11.5M Fund II, Proving Small Funds Can Deliver Big Wins (PR Newswire) Distributed to Paid-In Capital (DPI) definition SUBSCRIBE 📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📓 Substack: https://fundbuildscale.substack.com 📸 Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening! – Walter.

If a team hasn’t built a minimum viable product, secured paying customers, or demonstrated strong unit economics, what exactly are seed-stage investors betting on? To get some answers, I sat down with Nnamdi Iregbulem, a partner at Lightspeed Venture Partners, to discuss what drives seed valuations, the traits of successful founders, and his perspective on AI startups. “A lot of the pitches that I get are basically two people, a PowerPoint deck, and their dog,” Nnamdi told me during our conversation in October 2024. Nnamdi shared his journey from coding as a kid to investment banking at JP Morgan, growth-stage investing at Iconiq Capital, and now helping early-stage founders at Lightspeed. He explains why seed valuations often reflect the opportunity cost of the founding team more than traditional factors like interest rates or public market comps, and highlights the rising costs of GPUs and AI talent as critical considerations. We also explored the traits that set exceptional founders apart — like strong domain expertise, adaptability, and demonstrated excellence — and why inference-based AI startups may have an edge over those focused on training new models. For aspiring VCs, Nnamdi offers practical advice on developing domain expertise, building a network, and honing the skills needed to evaluate companies effectively. Whether you’re a founder, investor, or simply curious about the startup ecosystem, this episode is packed with actionable insights.   RUNTIME 33:24 EPISODE BREAKDOWN (2:24) “ I was the first-born son of two Nigerian immigrants who really badly wanted me to be a doctor.” (6:17) “ I was sort of like, ‘what do I know about early-stage companies?’ I never worked in a startup.” (8:50) The day-to-day work Nnamdi does with the founders in Lightspeed’s portfolio. (11:13) He explains why seed valuations aren’t valuations. (13:31) “ The only characteristic… that had any real predictive value was the opportunity cost of the founder.” (16:43) “ Coming from a large and stable big tech company is not the positive signal that it used to be.” (17:32) The weights and measures he uses to assess seed-stage founders. (19:33) When domain expertise is (and is not) useful. (20:53) How he evaluates technical vs. non-technical founders. (24:16) “A lot of the pitches that I get are basically two people, a PowerPoint deck, and their dog.” (25:18) How to pitch Nnamdi directly. (26:21) Setting valuations is “ more driven by the founders than it is by us.” (29:33) His advice for anyone who wants to break into venture capital. LINKS Nnamdi Iregbulem Seed Valuations Aren’t Valuations, whoisnnamdi.com email Nnamdi Lightspeed Venture Partners SUBSCRIBE 📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📓Substack: https://fundbuildscale.substack.com 📸 Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening! – Walter.

In the startups I worked at, we never had spare laptops.  When we hired someone, we’d order their laptop that day. That’s Startup Cashflow 101: don’t spend money until you have to. The same principle applies to your leadership team. Hiring a CMO before product-market fit? Too soon.  And a CEO can handle COO duties for a while. Most seed-stage companies don’t need a full-time CFO either.  A good controller can handle day-to-day finances, while a fractional CFO can plan future fundraising and create investor-friendly forecasts — all without reducing your runway. To understand why a fractional CFO might be the smarter move, I spoke to Dan DeGolier, founder of Ascent CFO Solutions. Runtime 27:21 Episode Breakdown (1:44) Dan explains Ascent CFO Solution’s origin story. (4:53) Why so many founders hire full-time CFOs before they actually need to. (6:33) A list of specific value-adds a fractional CFO can provide. (7:29) “We might be two days a week or three days a week. But we are very much a part of that team.” (8:57) Inside Dan’s client onboarding process. (12:44) “Part of it is getting a handle on cash flow and spend.” (15:24) “Understanding what the risk factors are to your runway is really critical.” (18:39) Which stats and KPIs are most important to share with the entire company? (20:51) If you want cash flow to break even, “be capital efficient to begin with.” (23:31) Clients “often supplement a VC round with a venture debt round so they can extend that runway a little bit further.” (25:09) How to interview a CFO if you don’t have an entrepreneurial background. (26:08) Resources Dan recommends for founders seeking financial discipline. Links Dan DeGolier Ascent CFO Solutions Good to Great: Why Some Companies Make the Leap...And Others Don't, Jim Collins Blue Ocean Strategy: How to Create Uncontested Market Space and Make Competition Irrelevant, W. Chan Kim and Renee Mauborgne Traction: Get a Grip on Your Business, Gino Wickman EOS One® Subscribe 📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📓Substack: https://fundbuildscale.substack.com   Thanks for listening! – Walter.

When I learned that MaC Venture Capital just raised $150 million for its third fund since 2020, I immediately reached out for an interview with Marlon Nichols, the firm’s co-founder and managing general partner. Marlon previously co-founded Cross Culture Ventures, which merged with M Ventures in 2019 to form MaC VC. In this interview, we talked about his path from enterprise software into venture capital, the concept of cultural investing, and MaC VC’s focus on diverse founders. He also explained what types of startups the new fund is open to and discussed some of the criteria he uses to assess the strengths of founding teams (and their ideas). Runtime: 45:44 Links Marlon Nichols Contact Marlon MaC Venture Capital Exclusive: MaC VC raises $150 million for its third fund in four years (Fortune) The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers, Ben Horowitz Secrets of Sand Hill Road: Venture Capital and How to Get It, Scott Kupor Subscribe 📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📓Substack: https://fundbuildscale.substack.com   Thanks for listening!   – Walter.

In this episode of Fund/Build/Scale, host Walter Thompson interviews Sahil Agarwal, CEO and co-founder of Encrypt AI. Sahil shares his journey from academia to leading an international AI company, discussing the importance of storytelling, confidence, and addressing biases within AI models. He also delves into challenges faced by immigrant entrepreneurs and the balance between leadership and employee well-being. Sahil provides insights into navigating enterprise AI security, fundraising strategies, and the intrinsic demands of running a startup. Tune in to uncover strategies for launching a company and overcoming industry hurdles. Runtime: 33:04 (1:46) Sahil describes Enkrypt AI use cases that “ensure equitable and safe use of AI for everyone.” (3:36) How his background in applied mathematics led to a career in enterprise security. (6:45) “You work until two in the morning whether that's PhD or a startup, and you wake up and you start again.” (8:34) “It took us some time talking to prospects and talking to people in the space to really hone in on the problem.” (11:42) Sahil’s path to obtaining the green card that would let him launch his own company. (15:31) “There has to be some sort of confidence that we have to project in front of investors and in front of enterprises or prospects.” (17:19) “You're accountable to everyone else in your company. That's my principle of leadership.” (20:26) How Sahil and co-founder Prashanth Harshangi approach work-life balance. (24:27) Setting expectations with investors and leading Enkrypt AI’s GTM strategy. (29:18) His advice for anyone pitching a seed-stage AI startup: “don't pitch a technology, pitch a story.” (31:17) The one question Sahil would ask an early-stage CEO if he were interviewing for a job. LINKS Enkrypt AI Sahil Agarwal, co-founder and CEO Prashanth Harshangi Enkrypt AI Raises $2.35 Million To Take On The Chatbots Going Rogue SUBSCRIBE LinkedIn Substack Thanks for listening! – Walter.

Branding is a condensed form of storytelling. That’s my opinion, but it’s also shared by David Placek, founder and president of Lexicon Branding. Here are a few of the companies and products they’ve named since 1982: Subaru Outback, Subaru Forester BlackBerry Pentium PowerBook Nissan Rogue Lucid Azure Sonos Swiffer NVIDIA Shield Febreze In May 2024, I interviewed him at his headquarters in Sausalito, California about brand architecture and positioning, the merits of being bold and authentic, and the methodology his company uses to transform innovative ideas into distinctive names that resonate.  Our conversation focused on aligning brand with market behavior, the art (and science) behind selecting a name, tools and exercises for brand identity creation, and techniques for validating a brand name before you commit to it. He also offered suggestions for early-stage teams on tight budgets and shared some insights from a study on branding for AI startups: “Don't overpromise, don't overhype, don't participate in all this hype.” RUNTIME 44:10 EPISODE BREAKDOWN (2:56) ”We have a process that takes that new idea and, and along the way, the goal is to give it a voice, a distinctive voice.” (4:02) How Lexicon Branding develops “coined” brand names. (7:18) Over time, David realized the company needed a creative layer and an engineering layer. (8:31) “Right now, in-house, we have at least three programs that are AI-based.” (10:22) “We are first and foremost a creative consulting firm, so everything has to be customized.” (12:09) David ballparks cost, timelines, and explains how Lexicon Branding works with clients. (15:07) “We create a vessel that will carry the story into the marketplace.” (17:36) How to validate your branding idea before fully committing to it. (21:53) Using generative AI in client work “is not only saving us time, but it's getting more information.” (25:07) Situations where David recommends changing your company’s name. (27:39) Head of Research Dmitri Seredenko offers an overview of an AI startup branding survey. (29:12) The challenge of injecting genuine emotion into your brand. (33:02) “I don't think any brands have really taken a stake on what they really want to be known for.” (35:56) “Don't overpromise, don't overhype.” (38:53) Why adding “AI” to your brand is a bad idea. (41:36) After you’ve made a decision, “stop trying to be comfortable about the new name.” (42:45) David describes the emotional experience of encountering his brands in daily life. LINKS Lexicon Branding David Placek Dmitri Seredenko 6 Things You Need to Know if You’re Building an AI brand SUBSCRIBE 📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/   📓Substack: https://fundbuildscale.substack.com   Thanks for listening!   -- Walter.

Deeptech founders are solving problems that most of us don’t think of as problems and tackling challenges that push the boundaries of what we think is possible. This interview with Justin Fiaschetti, CEO and co-founder of Inversion, is a good example. Inversion is building a platform that will enable space-based cargo delivery using autonomous re-entry vehicles with parachutes that will let them deliver goods from space to pretty much anywhere on Earth in less than 60 minutes within 20 feet of their customer. After my initial chat with Justin to prepare for this interview, I literally had to take a walk to process it all. Today, Inversion is announcing its $44 million Series A round — a clear signal that investors and potential customers believe the company is on the verge of something groundbreaking. “None of our customers care about how technically cool or what new fun technology we have on our product,” said Justin. “All they care about is can they get their cargo in under an hour, wherever they want. And so our goal is to do the minimum amount of technical innovation in order to meet our customers’ needs while having a growth path to continue to increase the capability [and] reduce the cost for our customers.” I interviewed him about early customer discovery and market validation, how Inversion is developing its go-to-market strategy, and asked how he plans to put the Series A to work in the company’s next stage of development. We also discussed the unique challenge of pitching something to investors that only exists in your imagination. “What is the addressable market for delivery from space? It doesn't exist right now,” said Justin. “Fundamentally, we're making a new market.” RUNTIME: 56:15 EPISODE BREAKDOWN (3:55) “Space really only has two viable business models. And we asked ourselves, ‘what's the third thing that's going to happen?’” (6:05) How Inversion’s on-demand space cargo delivery platform will work. (8:12) “I like to define ourselves by our customers rather than by our technology.” (12:08) “Having closed this Series A, there are a couple of big things for us.” (14:33) Differences between the Ray reentry vehicle and Arc, the larger prototype. (16:50) Inside Inversion’s go-to-market strategy. (20:39) “Nobody's built this before. There is no playbook. There is no rule set that you have to follow.” (25:21) Justin’s approach to validating customer demand for space-based cargo delivery. (27:40) “Our first investor pitch went terribly.” (31:07) Why Justin and Austin pivoted away from their initial idea. (34:40) “There is a huge market for on-demand and rapid cargo delivery.” (39:18) “We are the first new space company to develop parachutes in space.” (43:56) His framework for staying focused on product and customer needs. (46:00) “Starting with the military has been critical for us.” (50:45) “One of my personal goals is to deliver the Olympic torch.” (51:13) How Inversion is navigating the Valley of Death. (54:26) One question he’d have to ask the CEO if he were interviewing for a job at a deep tech startup. LINKS Inversion Justin Fiaschetti, CEO/co-founder Austin Briggs, CTO/co-founder Inversion Space accelerates orbital reentry vehicle tech with $71M Space Force contract (TechCrunch) Inversion secures reentry license for first mission (Space News) Jobs at Inversion SUBSCRIBE 📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📓Substack: https://fundbuildscale.substack.com   Thanks for listening! -- Walter.

If you want a healthy relationship, it’s essential to set clear expectations and boundaries from the start.  The same holds true for a founder and their board. Despite the power dynamics, CEOs can still create a transparent communication framework that respects everyone’s limited time. In part two of my interview with TigerEye co-founder and CEO Tracy Young, we discuss her approach to work-life balance, the unique challenges women founders face while fundraising, how to run a board meeting in 60 minutes, and the importance of gaming out worst-case scenarios. Runtime: 24:58 EPISODE BREAKDOWN (2:20) Why traditional 80-page board decks are “just not helpful for strategic discussion.” (5:32) How Tracy structures memos for board meetings. (7:18) The importance of gaming out worst-case scenarios with your team. (9:31) “Our motto is: ‘go towards where it hurts.’ Go fix it.” (12:40) Tracy and (co-founder/husband) Ralph’s approach to work-life balance. (15:26) “It's trite to say, but I try to meditate when I can.” (17:11) “I have met a lot of women founders who have told me horrific stories.” (20:24) “You look at who's writing the checks and are actually decision makers. They lean more towards male — actually white males.” (22:59) “You shouldn't be talking to customers in one meeting and in the same day meeting investors.” (23:48) The one question she’d have to ask a CEO if she were interviewing for a startup job. LINKS Tracy YoungWhy I started TigerEye Early-stage board decks are dead: How to run a meeting in 60 minutes TigerEye Ralph Gootee SUBSCRIBE 📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📓Substack: https://fundbuildscale.substack.com Thanks for listening! -- Walter.  

In 2011, Tracy Young co-founded PlanGrid, which made software for construction teams. After scaling the company to 450 people and raising $69 million, it was acquired by Autodesk in 2018 for $875 million. That’s a win, but Tracy and her partners didn’t go for the exit because they’d reached the peak of the mountain. They cut the deal because PlanGrid was behind in the market, and they didn’t know how to catch up. Three years later, during the pandemic, Tracy and her husband, Ralph Gootee, co-founded TigerEye, a RevOps AI agent that lets analysts answer questions and allocate resources based on data that’s updated multiple times each hour.  Last year, TigerEye closed a $30 million Series A. She describes it as “moneyball for business,” the tool she wished she’d had at PlanGrid when she was fighting entrenched competitors who were just better at enterprise sales.  In part one of our interview, she explains why they started their new company up in stealth and how TigerEye reflects her vision of what enterprise software should accomplish. She also shared what she’d learned as a CEO her second time around about building early teams and managing a hybrid workplace. Subscribe now to get part 2: Her approach to work-life balance The unique challenges women founders face while fundraising How to run a board meeting in 60 minutes, and The importance of gaming out worst-case scenarios. Runtime: 23:09 EPISODE BREAKDOWN (2:53) TigerEye’s origin story: “We wanted a second chance, and that became a big desire of ours.” (5:11) “There's certain decisions that only leadership and the CEO can make.” (7:58) “We just really sucked at selling to the enterprise.” (9:53) How to manage customer discovery while you're in stealth. (15:53) Tracy’s tactics for managing a remote-first team effectively. (19:25) When it comes to personnel, it’s “much harder to be mediocre at a small startup.” (21:21) Why she still interviews every new hire at TigerEye. LINKS Tracy Young Why I started TigerEye 5 failure points between 5 and 100M ARR  TigerEye Ralph Gootee SUBSCRIBE 📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📓Substack: https://fundbuildscale.substack.com Thanks for listening, -- Walter.