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.

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.

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

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

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.

In this 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!

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!

Imagine thinking your startup is doomed, only to be acquired for $165M. On this episode of High Stakes, Russ Heddleston shares the wild ride that led to DocSend’s $165 million acquisition by Dropbox. The absurd part? His investors doubted the product. Russ was left asking everyone, “Does anyone want to buy this company?” and heard nothing but no. Then Dropbox saw the value and made an offer of $165 million. Russ recalls, “We beat the IRR of every fund that invested in DocSend.” 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 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.

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.

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.

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.

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.

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.

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. 

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.

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.

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.

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.

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. 

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. 

In this episode, we dive into the do's and dont's founders should know while fundraising. To help dig into this topic are two members of the K Street Capital team, Nick Duafala, Principal, and James Culver, Associate. Tune in to gain the knowledge and strategies that can make a real difference in your startup's fundraising efforts. Whether you're a seasoned entrepreneur or just starting your journey, this episode provides essential guidance from the experts at K Street Capital.

In this episode of High Stakes, Paige Soya sits with Climate Tech pioneers Logan Soya and Kiran Bhatraju of Arcadia. Dive into an enlightening discussion about the confluence of Climate Tech and VC. Explore the intricacies of atoms vs bits investing and the burgeoning world of Climate Fintech. Discover the concept of transforming buildings into power plants and dissect the rise of SPACs in the sector. As both seasoned investors and groundbreaking founders, Kiran and Logan offer a unique dual-perspective on the challenges and opportunities of the current exit landscape. Tune in for a conversation packed with insights, trends, and expert advice.

In this episode of High Stakes, seasoned investors Ed Ingle and Jonah Seiger join Selena Strandberg, founder of "The Know", to delve deep into the realm of real-time employee sentiment analysis. As they weave through the intricate tapestry of venture capital, they shed light on the pivotal role such tools play for C-Suites, VCs, and startups. The discussion offers invaluable insights for both budding founders and astute investors. A must-listen for those eager to grasp the pulse of modern VC trends and the tech shaping them.

This episode addresses a question we’ve seen come up in popular media lately: Are startups dying and VCs backing away? To help answer this question are two members of the K Street Capital team, Nick Duafala, Principal, and James Culver, Associate. In their conversation, Paige, Nick, and James reflect on K Street Capital's unique investment philosophies and share insights from their firsthand experiences. Listeners will gain insights into whether startups are in fact facing challenges and if VC firms are becoming more cautious in their investments.

This episode focuses on future technologies for capturing attention and building relationships, with insights from two industry leaders from the K Street ecosystem: Sara Fagen, founder and CEO at Tunnl and K Street Capital investor; and Michael Barnett, CEO at InGo, a K Street Capital portfolio company. The conversation emphasizes the essential role of technology in capturing attention and creating authentic connections in today's digital world. This episode offers a comprehensive look at the event tech domain, bridging innovation and VC.

This episode explores property technology (proptech) solutions for decarbonization in commercial real estate. Featured in this episode are three industry experts from the K Street ecosystem: Aaron Block, Founder and CEO of Allumia, a K Street Capitalportfolio company; Alan Cohn, a K Street Capital investor, and Rich Thometz, also a K Street Capital investor. Join us as we delve into the latest technology advancements and practices that can help reduce carbon emissions in the real estate sector.

NFTs, Blockchain, and Web3: Key Insights for Founders and InvestorsThis episode explores the groundbreaking technologies of NFTs, Blockchain, and Web3. Featured in this episode are our expert guests Chris Brummer, law professor at Georgetown University; Robby Greenfield, CEO at Umoja Labs, a K Street portfolio company; and Amanda Wick, CEO at the Association for Women In Cryptocurrency and KSC member. Listen in as Chris, Robby, Amanda, and host Paige Soya demystify complex concepts; highlight how NFTs, Blockchain, and Web3 are shaping investment avenues and pivoting business strategies; and provide key insights for both newcomers and enthusiasts.

This episode dives into the topic of generative AI regulation. Featured in this episode are guests Jason Oxman, President and CEO of the Information Technology Industry Council (ITI) and K Street Capital investor; and Adam Boskovich, founder and CEO of WowYow, a K Street Capital portfolio company. Jason, Adam, and host Paige Soya discuss the impact of generative AI on VCs and startups, then go over the current landscape of generative AI policy initiatives, and also get into what investors and founders need to know when it comes to AI regulation.

recent release of the new $10B regional tech hubs program, an initiative born out of the CHIPS and Science Act, to create 10 tech hubs in US cities over the next 5 years. We talk about what the program is, how it works, what this means for the existing US tech industry and venture capital, and how cities and companies can benefit from the program. The discussion will include Blake Hall, the CEO/Founder of our portfolio company, ID.me, and his take on a potential cybersecurity hub; George Hornedo, one of our investors, who has been heavily involved in educating states and cities across the country about the program; and David Yarkin, the CEO/founder of our portfolio company, Procurated.

This episode is about the US Economic Development Administration’s

The vast capabilities of AI have changed the landscape of how technology is developed in behavioral science and edtech. We’ll discuss AI's influence on chatbots, and how this technology can improve outcomes for students. We’ll talk about how founders and investors in the edtech world are navigating this, how AI has changed in the recent past, and where it may be headed. Hear from 2 founder/CEOs with VC backed growth stage tech experience in behavioral science and edtech, one of whom has sat on both sides of the table as an investor and a founder.

This episode is about AI’s impacts on the travel industry as well as VC term sheet trends and how recent events/economic events (SVB, inflation, interest rates, public markets, etc.) have impacted terms. We’ll do some education on term sheets and various deal structures (SAFEs, convertible notes, and priced rounds), focusing on control terms, economic terms, and the expected future direction of valuation multiples. You’ll hear from one recently exited founder/CEO and one investor in the travel industry.

This episode is about how, when, why, and who to raise VC money from in 2023. With the explosion and confusion around AI technology enhancements, and the devastation of VC bank failures like SVB, First Republic – Many investors are sitting on the sidelines and the fundraising environment has changed materially. We’ll talk about how investors are navigating this, how founders should approach their fundraises, and tips for breaking through with a successful deal. Hear from 2 founder/CEOs with recent exits under their belts who have sat on both sides of the table as an investor and a founder.

This episode will cover the latest trends VCs need to know about how technology and regulatory changes will impact our ability to effectively communicate and influence. Think digital advertising, stakeholder decision making, company alignment, engagement, and productivity. We’ll dig in on two of the latest digital platforms taking advantage of these changes (AxiosHQ & Applecart) directly from their founder/CEOs.

This episode is about trends in digital credentialing, cyber security, and Web3 that are making headways in public-private sector pilots, projects, and operational business models. We will discuss federal, state, and provincial government policy, standards, legislation, and initiatives. We will also discuss the public benefit component of venture-backed investment in interoperable digital credentialing through commercial open-source software and open standards communities. Learn from 2 investor/founder/CEOs who are currently living and breathing these topics as leaders of a startup that is a leading developer of trusted digital ecosystems.

This episode is about the venture-backed mediatech space: Upcoming trends, today’s most scalable business models, the impacts of changing advertising regulation, and how these companies are using AI. We’ll also talk about how to employ mediatech in your own businesses from 2 experienced early-stage investors and one venture-backed mediatech CEO/founder.

This episode is a deeper dive into the latest developments of SVB & how they impact the VC ecosystem, access to capital, regulatory policy, and the future of how the banking world operates. We will also talk about how risk is getting repriced, the major transition away from easy money, why that’s a good thing, and what to watch out for from a fintech VC investor and a 2x founder/CEO.

This episode is about how VC investors evaluate cash flow & tips for when and how founders should make cuts in the current cash crunch environment. We will discuss burn, runway, RIFs, revenue reinvention and how to remain “default alive” from 2 founder/CEOs who have been through it and survived. We’ll also briefly discuss the impacts of SVB’s collapse on access to venture capital and debt.

This episode is about what makes a great founder and how investors evaluate founders and founding teams. We will discuss early indicators of a strong founder, the personality traits, perspectives, and abilities of strong founders, as well as how to evaluate and diligence a founder, red flags, and anecdotes from times when we read the signs right and wrong.