Episodes
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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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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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Episodes manquant?
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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
• embracing the shift to becoming an employee after a merger
Connect with us here:
1. Scott Tilton: https://www.linkedin.com/in/tiltcore/
2. Paige Soya: https://www.linkedin.com/in/paigesoya/
3. K Street Capital: https://www.linkedin.com/company/kstreetvc/
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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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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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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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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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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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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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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 insights underscoring the complexity and critical decisions involved in building lasting, impactful companies.
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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 challenges of lock-up periods, and strategies for managing concentrated positions post-exit. Tune in to Martin and Paige’s discussion on the dynamics of modern exit strategies and valuable perspectives for both founders and investors.
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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 realities of building and exiting successful tech companies.
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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 provide valuable insights for founders and investors alike.
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Step into the boardroom with host Paige Soya, seasoned public investor and former investment banker specializing in IPOs Rob Schwartzberg, and investment banker specializing in mergers and acquisitions Darren Womer as they discuss two paths that founders may ultimately find themselves deciding between: M&A or IPO. Drawing from their extensive experience and expertise, Rob and Darren offer listeners a behind-the-scenes look at both processes, sharing insider tips and practical advice for founders taking their businesses to the next level.
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In this episode of High Stakes, host Paige Soya chats with serial entrepreneur Rami Essaid about his journey founding, scaling, and ultimately exiting three successful companies. From paying his way through college selling cell phones in a mall to leading multimillion-dollar ventures, Rami's journey is marked by a series of strategic exits, each offering unique challenges and lessons. He candidly discusses the need for founders to keep doors open, maintain optionality, and prioritize strategic alignment when considering exit opportunities. Whether negotiating with investors, managing expectations, or planning for the future, his pragmatic advice serves as a guiding light for entrepreneurs navigating the complex landscape of exits.
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Explore the intersection of risk and reward in the cannabis industry with Mark Smith's candid account of one of his earliest investments. From early optimism to unexpected challenges, Mark shares the valuable lessons he learned while investing in a rapidly evolving industry and the resilience required to weather the storms of market volatility.
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Mei Xu's inspiring story is one of resilience, determination, and true entrepreneurial spirit. With candor and wisdom, Mei recounts the challenges and triumphs of navigating the sale of her business, providing a poignant glimpse into the emotional and practical complexities she encountered along the way. From managing the demands of chemotherapy to overseeing a high-stakes business transaction, Mei offers a compelling narrative of entrepreneurship as a journey of growth, discovery, and passionate pursuit of excellence.
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Join host Paige Soya and featured guests, Richard Leggett, former CEO of FrontierView and Tom McCormick, lead investor, as they discuss their highly successful exit after facing unprecedented challenges including the impact of the pandemic and rescuing the company from a potential fire sale offer. Rich and Tom offer candid insights into lesson’s learned and the importance of adaptation, resilience, and strategic decision making in a dynamic business environment.
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In this Season 2 premiere, host Paige Soya sits down with Roy Schwartz, exited founder/CEO of Axios, to discuss his journey through exits and entrepreneurship. The conversation highlights the complexities of acquisition deals, the rollercoaster of negotiations, and the importance of finding the right fit for both parties involved. Roy sheds light on the pivotal decisions that are made during the exit process, when to say no, when to say yes, and how to keep dialogue open and communication transparent so that acquirers and founders can align. His exit experience with Axios exemplifies how rewarding it can be to stay in the game until you find just the right buyer.
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Join us in the final episode of Season 1 of High Stakes as we delve into the vibrant world of Consumer Marketing and GTM strategies. Hear firsthand insights from Shizu Okusa, the visionary behind Apothekary's wellness journey; and Sahil Rahman, the co-founder of Rasa, who's charting new territories in the restaurant industry. Together with host, Paige Soya, they'll shed light on the challenges, innovations, and foresights of today's dynamic venture landscape.
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