High Stakes

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Podcast by Paige Soya

High Stakes

Join seasoned investors and successful start-up founders as they weigh in on topics and trends currently dominating the venture capital space. Each episode brings together a founder and an investor to provoke a deepened understanding of the topic at hand. If you want to learn about how early-stage venture capital investing works, this show is for you.

Latest episodes

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27 March 2025

How Government Policy Shapes VC-Backed Startups: Lessons from Softbank | Bruce Andrews

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:

  • Bruce’s background in government and commerce and his time at SoftBank.
  • How American policies compare with regulatory approaches in other countries, like China.
  • Challenges SoftBank successfully navigated when working with the US government.
  • Predictions for the new administration: potential regulatory changes and their effects.
  • How SoftBank helped companies by giving them access to a government affairs team.
  • What Bruce considers his biggest failure in the VC industry and what he learned from it.
  • Final thoughts from Bruce and the best advice he has ever gotten: “Be nice to everyone.”

Links Mentioned in Today’s Episode:

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13 March 2025

Fundraising from VCs: Game Changing Insider Tips | Basel Fakhoury

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:

User Interviews

Basel Fakhoury on LinkedIn

Basel Fakhoury on X

Entrepreneurs Roundtable Accelerator (ERA)

The Lean Startup

Paige Soya

K Street Capital

K Street Capital on YouTube

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05 December 2024

The End Is Not the End | Greg Vetter

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

Why Transparency Can Make or Break a Transaction | Dimitry Gershenson

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

How This Georgetown MBA Class Project Got Acquired by GoodBuy Gear | Alli Cavasino & Natalie Poston

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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24 October 2024

Leverage IP For A Winning Exit | Todd Bracher & Paige Soya

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 litigation attorneys

- making a product market-ready

Don’t miss out.

Connect with us here:

1. Todd Bracher: https://www.linkedin.com/in/toddbracher/

2. Paige Soya: https://www.linkedin.com/in/paigesoya/

3. K Street Capital: https://www.linkedin.com/company/kstreetvc/

Resources:

1. Design in Context (Todd’s book)- https://www.toddbracher.com/book

2. Market Efficiency Index (Free tool for founders/investors)- https://www.toddbracher.com/mei

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