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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26 September 2024

The Strategic Rationale Behind Early Exits | Aaron Mendes & PrivacyHawk

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 discuss everything from dead weight on your cap table, the need for a better understanding of liquidation preferences, and why you're better off selling early rather than too late.

Connect with us here:

1. Aaron Mendes: https://www.linkedin.com/in/mendes/

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

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

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45:40

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12 September 2024

M&A Lessons Every Entrepreneur Needs To Know | Richard Leggett & Tom McCormick

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 positioning for a successful exit.

With candid insights on resilience, timing, and critical decision-making, this episode is a must-watch for entrepreneurs facing tough choices.

Note: This episode is a re-upload with added substance and a quick sneak peak into the conversation at the start. Enjoy!

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43:00

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29 August 2024

3 Exit Strategies That Changed Everything, Featuring Zach Axelrod

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 maintaining control

Zach's candid insights on market timing, profit-taking, and strategic flexibility are pure gold. Don't miss this masterclass in entrepreneurial wisdom!

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25:30

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15 August 2024

How This Entrepreneur Sold His Startup To Dropbox For $165M | Russ Heddleston

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).

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29:03

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01 August 2024

Proactive Investment Exit Strategies: Insights from Marcus Brauchli

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 range of stories Marcus has to share on the importance of legal documentation, the complexities of international investments, and the various exit strategies companies may face. Marcus also emphasizes the necessity for founders to plan for exits from the beginning and maintain open communication with investors. Tune in for insightful advice on navigating the unpredictable landscape of venture capital exits.

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30:34

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18 July 2024

Industry Dive's Expansion Strategy and Exit with Founder Sean Griffey

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 Dive's subsequent acquisition by Informa in 2022, navigating the transition from private equity ownership to being part of a large public corporation, and the opportunities and challenges it brought.

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24:34