Fund/Build/Scale

2025 Cybersecurity Trends, Insights and Storytelling Advice from YL Ventures' Andy Ellis

In this episode of Fund/Build/Scale, I talked with YL Ventures Partner Andy Ellis (a former CISO) about his approach to storytelling, tactics for founder-led sales and marketing, and why he thinks the cybersecurity hiring challenge isn’t a talent shortage, but a market misunderstanding.
We also discussed refining product-market fit, customer discovery methods and pitfalls like believing in one's own narrative too strongly. The conversation also touched on hiring strategies, managing design partnerships, and maintaining humility as a founder. “The basic entry level skill of reading the room is knowing when somebody already agrees with you,” said Andy.
RUNTIME 44:15
EPISODE BREAKDOWN
(1:44) Andy describes his day-to-day work at YL Ventures with founders.
(4:08)  "It's like you now have an infant, and your only job as a parent is to create a competent adult.”
(6:33) How he prefers to be pitched.
(7:52)  ”The art of storytelling is taking a message and putting it in a narrative vehicle.”
(14:38) The biggest storytelling mistakes early-stage founders make.
(17:08) “ The basic entry level skill of reading the room is knowing when somebody already agrees with you.”
(18:50) “ Fear is a hard, hard sale… It's so transparent and CISOs do this every day.”
(19:36) Common cybersecurity GTM missteps.
(21:40)  ”The moment that you can sell the same product to two different companies, you should have a sales rep.”
(23:45) How Andy helps founders read the room when they’re trying to make a sale.
(27:20) “ You're hiring really out of a very different pool when you're in the cybersecurity space.”
(29:08) “ Stealth is sort of a misnomer, but we're still sort of stuck in it.”
(30:54) What to say if you want someone to quit their cushy job and join your risky startup.
(32:46)  Rock-star hires are “fantastic if they stumble into your lap, but you can't go look for them.”
(35:08) “ That first marketer you hire needs to be able to do a lot of things.”
(39:05) “People with massive egos have a lot of humility.”
(41:20) Trends in cybersecurity and AI he’s excited about in 2025.
LINKS
Andy Ellis
1% Leadership: Master the Small, Daily Improvements that Set Great Leaders Apart
csoandy.com
YL Ventures
YL Ventures’ The State of the Cyber Nation 2024 (PDF)
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Thanks for listening!
– Walter.

Lessons from Operant AI's Startup Journey: “ We're not wasting time on wheel spinning.”

Two of the three co-founders of Operant AI — CTO Dr. Priyanka Tembey and CMO Ashley Roof — joined me to talk about building the first runtime application protection platform and navigating the challenges of cloud-native security. The company announced a $10M Series A in September 2024 — In October, we discussed taking the leap into entrepreneurship, the lessons they learned through customer discovery and education, making early hires count, and the importance of early-stage team dynamics.
RUNTIME: 48:14
EPISODE BREAKDOWN
(2:28) “ I think it was within six months that we were able to have our first customer conversation.”
(3:46) What can customers do with a runtime application protection platform?
(9:38) “ What is interesting about our team is we don't come from prior security vendor companies.”
(12:59) Ashley explains how her first “real job” at Google eventually led her to Operant AI.
(15:51) “ I had many years of imposter syndrome to get over.”
(17:57) Why working with design partner teams is key, particularly for stealth startups.
(20:43) Priyanka discusses the company’s early customer education efforts.
(24:23) Ashley on why previous runtime application protection products hit “the trough of despair pretty fast.”
(28:26) Turning design partners into paying customers was part of their seed-to-Series A transition.
(31:04) Priyanka explains how Operant AI runs proof-of-concept programs for customers.
(34:28) Why they decided to start up in stealth.
(36:29) “ I honestly don't know how any consumer company could possibly start in stealth.”
(38:35) “ We have the technical leadership in place now… to scale the product further.”
(41:02) Inside their recruiting strategy and process.
(44:35) What’s changed since closing the Series A?
LINKS
Operant AI
Dr. Priyanka Tembey co-founder, CTO
Ashley Roof, co-founder, CMO
Operant AI Secures $10M Series A to Protect the Modern Cloud Across APIs, Applications and AI
SOC 2 compliance
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Thanks for listening!
– Walter.

Mercury Raise 2024 Survey: Founder Challenges, Fundraising Trends, and the AI Hype Cycle

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
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Thanks for listening!
– Walter.

Rusty Ralston and Jay Patil of Swell VC: A Hands-on Approach to Building Startups

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
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Thanks for listening!
– Walter.

Seed-stage Valuation Insights from Lightspeed's Nnamdi Iregbulem

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
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Thanks for listening!
– Walter.

Dan DeGolier: How Fractional CFOs Become a CEO's 'Strategic Teammate'

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®
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Thanks for listening!
– Walter.

MaC Venture Capital’s Marlon Nichols Offers Seed-stage Insights for Future CEOs

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
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Thanks for listening!
 
– Walter.

From PhD to CEO: Sahil Agarwal of Enkrypt AI Shares Essential Lessons for Aspiring Founders

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
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Thanks for listening!
– Walter.

Transforming Practical Wisdom into Iconic Brands with David Placek

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
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Thanks for listening!
 
-- Walter.

From concept to Series A: How Inversion got its space-based cargo platform off the ground

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
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Thanks for listening!
-- Walter.