High Stakes

Ever wonder why venture capitalists fight for board seats? It's not just about control or fancy dinners. In this episode, Paige Soya (Managing Partner, K Street Capital) sits down with Brian Goldsmith (Managing Partner, Avenue Growth Partners) to pull back the curtain on board governance in venture capital. In this episode, they cover the real work behind board seats, share war stories from boardr...

There’s a lot to love about working in venture capital but there’s also a lot of hard, often overlooked work that doesn’t make the headlines. In this debut episode of High Stakes , Paige Soya, Managing Partner at K Street Capital, sits down with James Barila, Former Revolution VC investor, now Executive Director at Station DC, for a candid conversation about the realities of running a venture fund...

What separates successful founders from the rest? In this episode of High Stakes , Paige Soya (Managing Partner, K Street Capital) sits down with Alex Wirth, CEO & Co-founder of Quorum, to unpack the habits, mindsets, and leadership lessons that helped him scale his company from 2 founders to 300+ employees over 10 years. Key takeaways: ✅ How to build the right team at every stage of growth...

In this episode of High Stakes, host Paige Soya sits down with Myrto Lalacos, Principal at VC Lab, for an in-depth conversation on landing a job in VC. Myrto shares her unique career journey—from leading accelerator programs in the UK to co-founding a B2B SaaS fund and launching the Venture Institute, an initiative aimed at connecting diverse, emerging talent with pathways into VC. Together, Paige...

What really happens when a startup shuts down? In this revealing episode of High Stakes, host Paige Soya sits down with Dori Yona, founder of SimpleClosure and seasoned entrepreneur, to unpack the complex—and often hidden—realities of shutting down a startup. After navigating the painful process of closing his own VC-backed company, Dori realized just how broken and opaque the process was, and bec...

Not every startup story ends in a big exit. Sometimes, despite best efforts, companies miss key milestones, burn through their runway, or become what investors call “zombie startups.” In this episode of High Stakes , host Paige Soya sits down with Tony Chan , partner at ORIC and seasoned venture capital and M&A expert, to explore the hard truths of venture investing. Tony shares insights into...

Why do some VCs lead while others follow? On this episode of High Stakes, host Paige Soya sits down with Mark Volchek, founding partner at Las Olas Venture Capital, to explore the dynamics of leading versus following in venture capital. With a focus on early-stage B2B software, Mark brings insights from his journey, from founding a FinTech company during the dot-com crash to launching and managing...

How do you make it in venture capital when the path is anything but straightforward? In this episode of High Stakes, Ethan Austin, Founding Partner at Outside VC, shares his journey and the key lessons he's learned as a founder in the world of early-stage investing. From the importance of empathy and people skills over traditional finance experience to the power of networking and taking bold, unco...

When choosing to invest in a company, there are a lot of elements for VCs to consider—and government policy is no exception. Today on High Stakes, we explore the role of government policy in venture capital and its impact on the industry. Joining Paige Soya to break it all down is Bruce Andrews, who has spent the last 30+ years at the intersection of business, public policy, and politics. Over his...

What would you do if you spent two years working relentlessly on a startup idea only to realize no one wants it? That’s exactly what happened to Basel Fakhoury before he and his co-founders scrapped their first business and pivoted to User Interviews, a platform that has now raised $45 million in venture capital. In this episode of High Stakes, Paige Soya sits down with Basel to break down what it...

In the final episode of Season 2, K Street Capital ’s Managing Partner, Paige Soya , sits down with Greg Vetter —the driving force behind Tessemae’s, one of the nation’s most iconic condiment brands. Greg unpacks the journey of growing a family business into a brand that was valued at $300M+ at its peak. From navigating the fallout of the pandemic to ultimately filing for Chapter 11, his story is...

In this episode of High Stakes, Dimitry Gershenson shares how his team tackled the operational and financial diligence required to pull it off, in this conversation K Street Capital’s Managing Partner, Paige Soya . Dimitry reflects on the challenges of validating key information, noting that diligence often means asking the same question in multiple ways to uncover inconsistencies. They discuss th...

What started as an MBA class idea led to an acquisition by one of the nation’s leading baby and kid gear marketplaces. Alli Cavasino and Natalie Poston , founders of JoyLet , built a no-frills “rent-the-runway” model for baby gear, allowing parents to rent items for the time they need. In EP 19 of High Stakes, Alli and Natalie join Paige Soya , Managing Partner of K Street Capital , to discuss the...

How do you leverage intellectual property for M&A? In this episode of High Stakes, Todd Bracher joins Paige Soya to answer. With over 20+ years experience in building great products, Todd believes that the world’s biggest problems already have solutions, but they need the right design approach to shine. They discuss: - how better design can give your patent the moat it needs - TRLs and IP liti...

Hookit was acquired by KORE Software for much more than the $20 million they raised over three funding rounds. But getting there was no walk in the park. In this episode of High Stakes, K Street Managing Partner Paige Soya is joined by Scott Tilton , exited co-founder of Hookit. They discuss: • how Hookit got acquired for 2x the offer price • why co-founders need to be aligned before the big close...

Managing our digital footprints has become almost impossible without the right tech. Personal data is more vulnerable than ever, and cybercriminals are ready to take advantage. That’s where PrivacyHawk steps in — your defense against this growing digital chaos. We're thrilled to have backed PrivacyHawk in its recent $3M funding round. In this conversation with Aaron Mendez , CEO of PrivacyHawk, we...

Building a company for exit? Prepare for the long haul. In this encore episode, hosted by Paige Soya , Richard Leggett , former CEO of FrontierView, and lead investor Tom McCormick dive into the harsh realities of the world of M&A. They share how they navigated the pressures of competing priorities, kept the business afloat during the pandemic, and avoided a fire sale by strategically position...

In this episode of High Stakes, host Paige Soya dives in with Zach Axelrod, CEO of Redball Energy, uncovering the game-changing moments that shaped his entrepreneurial success. Discover: • How financial leverage and perfect timing led to Zach's career-defining $100M exit • Insider tips on maximizing returns from high-growth investments • Crucial lessons on negotiation power dynamics and maintainin...

Imagine thinking your startup is doomed, only to be acquired for $165M. On this episode of High Stakes , Russ Hiddleston shares the wild ride that led to DocSend’s $165 million acquisition by Dropbox. In this chat with Managing Partner Paige Soya, they discuss funding, exits, Russ’s next venture, Distill (hint: think Wikipedia but for company and people summaries).

In episode 12 of High Stakes, Paige Soya, Managing Director of K Street Capital, interviews Marcus Brauchli, co-founder of North Base Media and former managing editor at the Wall Street Journal, on the intricacies of investment exits. Marcus shares his extensive experience in the venture capital world, highlighting the lessons learned from both successful and failed exits. They cover the wide rang...

In Episode 11 of High Stakes, Paige Soya interviews Sean Griffey, CEO of Industry Dive. Griffey discusses Industry Dive's journey from bootstrap beginnings to a company with $100 million in revenue and over 400 employees, culminating in its acquisition by Falfurrias Capital. He emphasizes the importance of preparation and cultural fit in acquisitions. Griffey also shares insights into Industry Div...

In episode 10 of High Stakes, Paige Soya, Managing Partner at K Street Capital, and Joe Fluet, Founder of Fluet Law Firm and MAG Aerospace, discuss Fluet’s journey from founding MAG to navigating significant exits and recaps. He emphasizes a values-driven approach to business, discussing how aligning with investors who share these values is crucial for long-term success. Tune in to hear Fluet’s in...

Join us as we dive into the world of multiple exits with Martin Tobias, Managing Partner of Incisive Ventures. Martin brings a wealth of experience and perspective as a GP and a three-time venture-funded CEO who has navigated IPOs and strategic acquisitions, sharing insights from his journey with Loud Eye Technologies, among others. He discusses the nuances of laddering and IPO pricing, the challe...

Political operative turned tech entrepreneur, Sara Fagen, shares a wealth of knowledge in this episode of High Stakes. Join us as Sarah and host Paige Soya discuss lessons from raising venture capital, timing an exit, the dynamics of venture-backed versus self-funded businesses, and strategic reasons behind acquisitions in the tech industry. Throughout the conversation, Sarah reflects on the reali...

Join us as we sit down with Hans Miller, founder of Airside, a pioneering company in the digital identity and travel space, to explore his strategic exit during the COVID-19 pandemic. Hans shares how the pandemic reshaped Airside's trajectory, and offers lessons learned for startup founders and his perspectives on the future landscape of digital identity in travel. Hans's candid reflections provid...