Podcast by Paige Soya
11 April 2025
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, unconventional actions to set yourself apart, Ethan breaks down what it takes to succeed in VC. He also reveals why storytelling, strategic name-dropping, and putting your own capital on the line can make all the difference in your career. Whether you're looking to break into the industry or refine your approach, Ethan's insights will help you navigate the highs and lows of venture capital success. Tune in to learn how to leverage relationships, embrace failure, and become a smarter, more resilient investor!
Key Points From This Episode:
• No straight path: a founder’s guide to a career in early-stage venture capital.
• Why empathy and people skills matter more than traditional finance experience.
• The power of networks: how relationships open doors.
• How the best investors assess risk, luck, and opportunity.
• Key traits of successful VCs, including dedication, creativity, and resilience.
• Insight into what it really takes to break into the venture capital world.
• Taking bold, unconventional action to stand out from the crowd.
• The magic of winging it, embracing failure, and just making the leap.
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27 March 2025
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 career, he’s occupied a range of consequential roles, both in government and commerce, from Deputy Secretary of the US Department of Commerce to Vice President for Global Public Policy at SoftBank. Bruce unpacks the ways government policies affect VCs, how a change in administration can impact startups, and what companies should do to prepare. He sheds light on his time at SoftBank and what it taught him about the VC industry before expanding on how the company helped startups by giving them access to government affairs experts. We also hear Bruce’s reflections on failure and success, his advice to listeners, and more. Join us for a fascinating exploration of government policy and its impact on the industry of venture capital!
Key Points From This Episode:
Links Mentioned in Today’s Episode:
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13 March 2025
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 really takes to raise money from VCs, from navigating rejections to mastering the fundraising narrative. They cover the art of building investor relationships (spoiler alert: it’s a long game!), the must-have data points and deal terms that can make or break a pitch, why a strong financial story matters just as much as traction, and how User Interviews transitioned from a scrappy Craigslist hustle to a SaaS powerhouse. Plus, Basel shares the biggest mistake he made as a founder and the fundraising strategy that changed everything.
Key Points From This Episode:
• Focusing on things you can control: what it takes to raise venture capital.
• What investors actually look for and how to make it easier for them to say yes.
• The psychology behind a VC’s biggest fear (and how to leverage it).
• Why warm introductions and investor networks are crucial.
• Reasons that transparency and consistency are key in VC due diligence.
• Red flags that make term sheets a dealbreaker for founders and funders.
• One thing that VCs really want to know: can you do it again?
Links Mentioned in Today’s Episode:
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05 December 2024
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 one of grit and perseverance.
He also opens up about his new book, “Undressed: The Unfiltered Story of My Failed American Dream and How It Led to Success,” offering a candid look at the lessons learned along the way.
A fitting close to a season all about exits—don’t miss this one.
Greg’s book- https://www.amazon.com/Undressed-Unfiltered-Failed-American-Success/dp/0960127704
Connect with us here:
1. Greg Vetter: https://www.linkedin.com/in/gregvetter/
2. Paige Soya: https://www.linkedin.com/in/paigesoya/
3. K Street Capital: https://www.linkedin.com/company/kstreetvc/
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22 November 2024
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 the importance of trusting your instincts during the diligence process and how open, honest communication can make or break a successful transaction.
Connect with us here:
1. Dimitry Gershenson: https://www.linkedin.com/in/dgershenson/
2. Paige Soya: https://www.linkedin.com/in/paigesoya/
3. K Street Capital: https://www.linkedin.com/company/kstreetvc/
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07 November 2024
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 exit and how they navigated the roadblocks in their journey.
Connect with us here:
1. Alli Cavasino- https://www.linkedin.com/in/allicavasino/
2. Natalie Poston- https://www.linkedin.com/in/natalieposton/
3. Paige Soya: https://www.linkedin.com/in/paigesoya/
4. K Street Capital: https://www.linkedin.com/company/kstreetvc/
00:00 Introduction
00:47 Meet the Founders: Ali and Natalie
01:41 The Birth of Joylette
04:41 Early Challenges and MVP Development
05:38 Raising Capital and Going Full-Time
07:31 Learning and Pivoting the Business Model
09:34 Customer Acquisition Strategies
16:43 Deciding to Exit
19:34 The Exit Process
24:43 Reflections and Future Plans
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