Fund/Build/Scale

Journey founder and CEO Stephen Sokoler appeared on Fund/Build/Scale in June 2024 to talk about how his startup pivoted from B2C meditation services to a B2B mental health platform, along with what that shift revealed about selling to enterprise clients. He breaks down the challenges of high customer acquisition costs, the trade-offs of venture capital, and the key lessons founders should know before making a major business model shift. RUNTIME 38:28   EPISODE BREAKDOWN (2:20) Why Stephen decided to found Journey — identifying the need for accessible mental health solutions. (5:07) “We probably had five or six different products that worked and didn't work until we got to where we are today.” Lessons from early iterations and failures. (7:32) Pivoting to B2B “was definitely a safer bet than to continue doing consumer, which just seemed like a dead end.” (9:26) Landing early customers like Warby Parker — how this helped de-risk Journey for enterprise clients. (11:37) Why he sought out venture capital in the company’s early days — and what he learned from the process. (13:56) Knowing what he knows now, would he still have pursued VC? (17:11) Reaching product-market fit “changes the fundamentals of the business significantly.” (19:00) “One of our core pillars is that it's a global offering rooted in diversity and inclusion.” (23:17) We think it's really important to make mental health part of the fabric of working at a company, versus a random benefit.” (25:17) The three key data points Journey tracks to measure impact and effectiveness. (28:25) “You can decide: Do you want it to be a lifestyle business? Do you want it to be a unicorn?” (31:49) Work-life balance vs. work-life integration — “I don't like the term ‘work-life balance,’ because then it feels like something's always kind of out of whack.” (34:29) How Stephen has learned to manage the mental toll of entrepreneurship. (37:25) “Not every business should be a venture-backed business.” Key insights on whether VC is the right path. LINKS Stephen Sokoler Journey   SUBSCRIBE   🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/fund-build-scale/id1719488387 🎧 Spotify: https://open.spotify.com/show/0EbC8PTUSfpZ4USPC9ErnN 📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📓Substack: https://fundbuildscale.substack.com 📸 Instagram: https://www.instagram.com/fundbuildscale/   Thanks for listening! – Walter.

When you accepted the offer, maybe you imagined being in the group photo when your boss rang the bell at NASDAQ. But five years later, your company just raised its Series C, and an IPO isn’t on the horizon. Meanwhile, you need liquidity — whether it’s for a down payment on a house, starting a family, or another major life event. The stock options you’ve earned are fully vested, but they’re just sitting there. So how do you turn them into cash? If your company allows it, you can sell your shares to an accredited investor, assuming you can find a buyer who’ll meet your price. That’s where the secondary market comes in. I spoke with Phil Haslett, founder and Chief Strategy Officer at EquityZen, a platform that helps startup employees sell a portion of their equity to investors looking to get in on high-growth companies before they go public. We took a deep dive into how the secondary market works, its risks and rewards, and how aspiring founders can even use it to bootstrap their own startups. Disclaimer: This interview is for informational purposes only. Nothing Phil says should be interpreted as financial advice. RUNTIME 41:54 EPISODE BREAKDOWN (0:00) I used Descript to create an elaborate cold open for this episode, please listen. (3:19) The specific pain point that led Phil and Atish to start EquityZen. (5:11) “ I've kind of gone through maybe two or three evolutions of the IPO markets since EquityZen started.” (7:57) All things being equal, early-stage tech workers take on more risk than founders or investors. (9:12) Few workers are well-informed about the secondary market, “but it’s not their fault.” (11:38) “ At some point, employees start to decide that maybe where they want to work — or maybe where they want to keep working — might be informed a bit by what they can or can't do with their equity.” (13:06) Should we keep the traditional four-year vesting schedule, or scrap it for something new? (14:14) Typical reasons why sellers turn to the secondary market. (16:25) EquityZen’s typical selling size and average investment size, as of November 2024. (18:52) ” You're probably not gonna get a billion-dollar valuation for your shares purely based on structure alone.” (20:45) Keep close track of your equity, especially if you think you’re going to be laid off. (22:20) Consult a financial services professional before you start the process. (24:16) “ The first steps are kind of just also learning if you can sell your shares.” (27:04) “ The company that you held shares in, if it went to zero: would you regret that you didn't sell?” (30:10) A framework for figuring out whether the secondary market is worth the time and trouble. (33:25) Offer your employees liquidity without jeopardizing morale or financial stability. (36:27) Phil’s founder pitch: “ We're gonna support you all along the way. We can help you with liquidity in the future.” (39:16) Tips for approaching your CEO to ask about liquidity options. LINKS Phil Haslett, co-founder/Chief Strategy Officer Atish Davda, co-founder/CEO EquityZen Descript stock library: Music: She Was In Hawaii (Lap Steel) SFX: Bar Background Ambience 01 SFX: Ocean Waves Crashing Ambience SUBSCRIBE 🎧 Apple Podcasts: https://podcasts.apple.com/us/podcast/fund-build-scale/id1719488387 🎧 Spotify: https://open.spotify.com/show/0EbC8PTUSfpZ4USPC9ErnN 📥 LinkedIn:https://www.linkedin.com/newsletters/7249143254363856897/ 📓Substack: https://fundbuildscale.substack.com 📸 Instagram: https://www.instagram.com/fundbuildscale/ Thanks for listening!   – Walter.

Do you want to know the difference between marketing and PR? Marketing is when you say something nice about yourself; PR is when other people say nice things about you. Jenna Guarneri is the founder of JMG Public Relations and author of the bestseller "You Need PR." In this episode, she shares DIY PR tactics that help founders establish themselves as experts, attract customers, and raise their profile with investors — without spending a fortune on an agency. If you’ve ever wondered why reporters never get back to you, we cover that, too. Key takeaways from this episode: ✅ Why PR comes before PMF in the startup playbook ✅ The biggest PR misconceptions founders have (and how to avoid them) ✅ How to craft a media pitch that actually gets responses ✅ DIY PR strategies for building credibility before you hire a firm ✅ The right way to engage with journalists without being ignored ✅ How PR can help secure funding and drive startup growth If you’re trying to take control of your PR strategy and attract positive attention, listen in. RUNTIME 31:28 EPISODE BREAKDOWN (1:52) How Jenna sets client expectations on what PR can and cannot accomplish. (5:14) Key signals that indicate an early-stage startup is ready to hire outside PR. (6:41) “The founders usually are amenable to PR and doing media interviews. It kind of comes with the territory of being a founder.” (7:59) How to get started with DIY PR by sharing thought leadership that creates value. (11:35) “PR should be done at the very beginning, right from the very start.” (12:20) The right way for stealth startups to approach PR. (13:02) The top reasons why reporters ignore pitches — and how to avoid them. (15:21) Crafting a news hook that genuinely engages journalists. (17:33) How your world changes when PR starts working. (18:50) “Effective public relations will drive the business in a number of ways.” (20:50) How to interview and vet a PR firm before making a commitment. (22:46) PR is a long game: “We can't work miracles in three months.” (25:22) Why using ChatGPT to pitch reporters is a terrible idea. (27:42) “Content creation does take a lot of time, a lot of energy, but it goes a long way really quickly for brand awareness.” (30:14) The one question Jenna would have to ask before hiring a PR firm. LINKS Jenna Guarneri JMG Public Relations You Need PR SUBSCRIBE 📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📓Substack: https://fundbuildscale.substack.com 📸 Instagram: https://www.instagram.com/fundbuildscale/ Thanks for listening! – Walter.

Building a startup in Africa isn’t the same as doing it in Silicon Valley. Some challenges overlap, but many don’t, like currency volatility, limited early-stage funding, and investors who expect you to scale faster than the market allows. So how do you grow beyond your home market? How do you raise funds when VC is scarce? And what do African founders need to do to make their startups more venture-backable? To find out, I spoke with Mobola da-Silva, a partner at Capria Ventures who’s based in Nairobi, Kenya. She’s been investing in Africa and other emerging markets for nearly two decades and knows exactly what separates startups that thrive from those that stall. She shares practical insights on navigating currency risk, securing funding, and preparing for Series A — even if you don’t have a deep-pocketed network to lean on. If you’re an African founder trying to build a company that investors take seriously, this episode is for you. RUNTIME 46:19 EPISODE BREAKDOWN (2:03) How Mobola got her start in VC and the path that led her to Capria Ventures. (4:09) Capria Ventures' investment thesis. (5:32) The regions and sectors where generative AI is creating real value. (10:41) The best way to pitch Capria Ventures — and what investors want to see. (12:26) “A venture-backable business has to be able to achieve significant scale.” (15:13) “We're getting a bit more creative in Africa around funding for startups.” (16:20) How currency volatility impacts valuations — and strategies for mitigating risk. (22:18) “To pitch successfully, you have to be able to tell a story, right?” (23:51) Why Capria Ventures avoids solo founders and what investors look for in teams. (28:33) “Many investors don't think of product-market fit as a binary thing.” (31:29) The key metrics that signal true product-market fit. (33:49) “Make sure that you have a strong business before you try to start to move it to another market.” (37:49) “Silicon Valley looms larger than life in Africa.” How founders should interpret this influence. (42:46) Mobola’s top advice for early-stage founders in Africa looking to scale and raise capital. LINKS Mobola da-Silva Capria Ventures Investment inquiries SUBSCRIBE LinkedIn Substack Instagram Thanks for listening! – Walter.

Eric Ly is the CEO of KarmaCheck, where he’s tackling a problem he first noticed years ago as a co-founder of LinkedIn: People don’t always tell the truth about themselves. To address this, KarmaCheck — launched in 2019 — automates key aspects of the background check process. By reducing complexity, employers can speed up hiring, while job applicants experience less friction along the way. “This is one of the first touch points with the employer: experiencing pain and frustration having to go through this process,” said Eric. “For us to show up with something new and different and better was frankly a breath of fresh air for the employers, the customers that we work with.” In this episode, we discuss: Jumping into a highly regulated industry with no prior domain expertise Why customer discovery should focus on patterns, not one-off insights The benefits of selling new features before they exist How to balance customer requests without losing focus We also talk about stepping out of LinkedIn’s shadow, resisting the temptation to build for a single customer, and knowing when to say “no” to feature requests. RUNTIME 40:20 EPISODE BREAKDOWN (1:37) “Several years ago, I became really interested in this whole concept around trust and trust online.” — How Eric first recognized the problem that led to KarmaCheck. (3:22) Entering a highly regulated industry without prior experience — where Eric found the confidence to take the leap. (5:30) A look back at KarmaCheck’s first hires — who they brought in early and why. (6:47) How KarmaCheck convinced early customers to take a chance on an unproven solution. (10:36) “Where employers don't even meet the people that they interview in person, there's an opportunity for the wrong things to happen.”  (12:21) “We identified a pain point in corporate America that people often experience frustration with.”  (14:34) How Eric used early customer feedback to shape KarmaCheck’s product strategy. (16:11) The role of proof-of-concept programs in building customer trust. (21:16) “Make sure that whatever you commit to in your product is going to be applicable for more than one customer.”  (24:47) When customer feedback leads you down the wrong path — how to recognize it and recover. (27:46) Why it’s important to keep track of rejected product ideas.  (29:49) The lessons from LinkedIn that Eric chose not to apply at KarmaCheck. (32:54) Advice for founders who want to step out of a shadow and build something completely new. (35:54) How to find a mentor when you don’t have a built-in network — Eric’s tips for making meaningful connections. (38:24) The one question Eric would ask a CEO if he were interviewing for a job at an early-stage startup. LINKS KarmaCheck Eric Ly KarmaCheck Raises $45 Million Series B to Modernize Background Checks and Credentialing (Press release. 6/27/2024) SUBSCRIBE LinkedIn Substack Instagram Thanks for listening! – Walter.

Most early-stage founders I talk to are focused on getting their first customers, hiring their first employees, or maybe, if they’re lucky, closing their first round of funding. But what happens after that? For Rohit Choudhary, the answer was building a whole new category. Rohit is the CEO and co-founder of Acceldata, a data observability platform that helps companies manage the complexity of modern data infrastructure. Before starting the company, he spent years inside the problem — working on data engineering challenges at Hortonworks and other enterprise tech firms. Like a lot of technical founders, Rohit didn’t start out dreaming of being a CEO — but the problem was too big to ignore. In this episode, we talk about: Why data engineering lacked the right tooling and how that led to Acceldata How his team validated the concept with real-world customer pain points The trade-offs of building in stealth mode vs. in public What he’s learned about hiring, scaling, and making the leap from engineer to CEO If you’re trying to figure out how to go from technical insight to scalable business, this one’s for you. RUNTIME 37:37 EPISODE BREAKDOWN (2:16) “ There are four of us co-founders, and we were all part of the same engineering team at Hortonworks.” (4:33) “ We felt that here was a unique opportunity for us to be able to build something really, really large and big.” (6:16) How Acceldata approached proof-of-concept programs in its early days. (8:23) “ How did you decide which one of you would become the CEO?” (11:31) Rohit’s seed-stage recruiting strategy: “ we had to excite them with the long-term vision.” (14:35) “ People like me, we learned how to sell despite coming from an engineering background.” (16:46) Why the co-founders “took a leap of faith” by formalizing their sales process early. (18:46) “ We were familiar with how business is conducted in the U.S.,” which made expansion easier. (21:08) Early challenges they faced after closing a Series A. (23:08) How “a big mistake” from a previous startup still influences Rohit’s choices today. (25:30) Wondering if it’s time to throw in the towel? Do a self-assessment. (28:31) Three core skills engineers need to acquire if they want to become effective CEOs. (31:39) “ I used to interview almost everyone until we were at about, you know, 170-180.” (33:82) How creating a 10-year strategy informed their day-to-day decision making. (36:27) The one question he’d have to ask the CEO in an interview before he could accept an offer. LINKS Acceldata Rohit Choudhary, co-founder/CEO Ashwin Rajeeva, co-founder/CTO Gaurav Nagar, co-founder/Senior Architect Raghu Mitra Kandikonda, co-founder/Director of Engineering Lightspeed Venture Partners Acceldata Announces $50 Million in Series C Funding to Expand Market Leadership and Product Innovation in Data Observability (press release) SUBSCRIBE LinkedIn Substack Instagram Thanks for listening! – Walter.

Startups face unexpected risks every day — cyberattacks, lawsuits, market shifts —but many entrepreneurs don’t think about risk management until it’s too late. In this episode of Fund/Build/Scale, Vouch co-founder/CEO Sam Hodges explains why risk management should be top of mind for early-stage founders. We discuss: Why risk management matters for early-stage startups   How Vouch validated, built, and launched Corix as a new business unit   The biggest mistakes founders make when managing risk   Why work-life balance is a myth for startup leaders   Key insurtech trends that early-stage founders should watch in 2025   Sam also shares insights on team structuring, branding, and time management—plus the one question he’d ask an insurtech CEO before taking a job. RUNTIME: 44:36 EPISODE BREAKDOWN (2:27) “ Risk management is something that a lot of founders don't think about a lot, but when it matters, it really matters.” (3:26) How Sam connected with co-founder Travis Hedge. (5:53) Why Vouch’s first team member was a design lead. (6:35) What sets Corix apart from Vouch’s core offerings. (9:05) The process behind starting up a new business unit. (12:42) “ At some point in scale, almost every company is going to organize around products, geographies, or market segments.” (15:05) “ There are three very specific stakeholder groups that we talk to all the time.” (16:26) How the team balanced quantitative metrics against qualitative insights while planning. (18:50) Inside their messaging, branding and rollout strategy for Corix. (21:59) “ The roots of Corix are ‘core’ and ‘risk,’ and we really do think that's what this is all about.” (25:47) How Sam’s day-to-day work is different since launching a new BU. (28:25) A few thoughts about time management and self-care. (30:32) “ I am not a big fan of the term ‘work-life balance.’” (33:22) “ When you make a decision like this, it is going to always feel like it is too early or too late.” (35:48) Insurtech trends early-stage founders should look out for in 2025. (40:14) The biggest risk-management mistakes Sam sees founders making. (43:14) The one question he’d have to ask an insurtech CEO if he were interviewing for a job. LINKS Vouch Sam Hodges, co-founder/CEO Travis Hedge, co-founder/CRO Introducing Corix: An MGA from Vouch, Empowering Brokers with Tailored Insurance Products (PR Newswire) SUBSCRIBE LinkedIn Substack Instagram Thanks for listening!   – Walter.

Amr Awadallah is the CEO and co-founder of Vectara. Previously, he co-founded Cloudera, which went public in 2017 and was acquired for $5.3 billion, and also served as VP of Developer Relations at Google Cloud. His first startup, Aptivia, was acquired by Yahoo, where he later became VP of Product Intelligence Engineering. I talked to him about his experience as an immigrant in Silicon Valley, the frameworks he’s built to articulate vision and credibility, and what he’s learned about pitching investors and recruiting top talent over the years. Runtime: 52:43 EPISODE BREAKDOWN (3:39) “ The more technical definition of what we do is ‘RAG as a service.’” (5:38)  ”You ask your car, ‘why is this icon showing, what's wrong with you?’ And the car will tell you, hey, you need to go change my oil.’” (8:07) What makes Vectara a blue-ocean company. (10:05) How to win an investor’s confidence when your current TAM is zero. (12:04)  ”There's three things anybody looks for when they're going to join any job, and you need to at least win two of the three.” (15:06) How Amr connected with the other Vectara co-founders. (17:24) Why he’s “a very big opponent to building in stealth.” (21:50) Attending Stanford helped Amr visualize himself as an entrepreneur.  (24:34) “ Many entrepreneurs think that the idea is what's going to make a company succeed or not.” (28:54) How he cultivated an appetite for risk again after spending eight years at Yahoo. (32:44) “ Only get the PhD in one case, and one case only: if you want to be a professor.” (37:35) “ By definition, more immigrants will be more willing to take risks.” (41:33) “ There's so many VCs out there pretending they're amazing.” (43:54) There are two types of salespeople: “coin operators” and “innovators.” (48:20) You can start up outside Silicon Valley, but “ if you can move here, move here.” (50:27) Two questions he’d ask the CEO if he were interviewing for a job with a new startup. LINKS Amr Awadallah Vectara Cloudera Google Cloud SUBSCRIBE LinkedIn Substack Instagram Thanks for listening!   – Walter.

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) SUBSCRIBE TO FUND/BUILD/SCALE LinkedIn Substack Instagram Thanks for listening! – Walter.

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 SUBSCRIBE LinkedIn Substack Instagram Thanks for listening! – Walter.