#dreamitlive by Charles LaCalle

Last Updated: May 3, 2026
Watch founders, operators, venture investors, and others discuss issues around scaling startups, fundraising, marketing, and selling to enterprise customers.
M&A Insights: How, Why & When Startups are Acquired
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When speaking to nearly all startups about their exit strategy, it almost invariably is acquisition. But startup M&A is an area most founders know very little about and is clouded in mystery. What really happens when a startup is acquired, how does it happen, and when? Who reaches out to whom? Do you need a banker or boutique M&A firm? What are the tricks and traps on both sides of the table?
JetBlue Chairman Joel Peterson: Building Trust in Remote Workers, Entrepreneurial Leadership, and Resilience
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Joel Peterson is Chairman of JetBlue Airways and a professor at Stanford's Graduate School of Business. After three careers, four decades of marriage and seven kids, and demanding roles as CFO, CEO, chairman, lead director, adjunct professor, founder, author, entrepreneur and investor, Joel Peterson is often sought as a mentor and coach by leaders and aspiring leaders.  
Steve Case: The Future of Work and Entrepreneurial Ecosystems Post-Pandemic
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Startup Challenges and the Future of Work Steve Case is one of America’s best-known and most accomplished entrepreneurs and a pioneer in making the Internet part of everyday life. In 1985 he co-founded America Online (AOL), which became the world’s largest and most valuable Internet company, helping to drive the worldwide adoption of a medium that has transformed business and society. For the past 15 years, Steve’s focus has been on starting and scaling https://www.revolution.com/ (Revolution), the Washington DC-based investment firm that backs entrepreneurs at every stage of their development through Revolution Growth, Revolution Ventures, and Revolution’s Rise of the Rest Seed Fund, which has invested in more than 140 startups in over 70 U.S. cities.
Annie Duke: Decision-Making Tactics, Embracing Uncertainty, & Cognitive Bias in Startups
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In this #DreamitLive https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions/dp/0735216355 (best-selling author) and former professional poker player Annie Duke (https://twitter.com/AnnieDuke (@AnnieDuke)) explains how mental models, decision-making tactics, and behavioral science can help founders make better decisions as they build and scale their companies. Particularly during these challenging times, founders and startup employees face uncertainty every day. And the best founders, like the best poker players, have a process for embracing uncertainty in decision-making, learning from successes and mistakes, and recognizing (and removing) inherent biases. With her background in high-stakes poker coupled with her research and writing on psychology, economics, game theory, and neuroscience, Annie and Steve will discuss tactical ideas for founders to improve their decision-making skills. 
Motivating and Managing Startup Teams During a Pandemic
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Sarah Pillmore is the former VP of human resources and talent acquisition at two of Expedia Group’s premier brands, Hotwire and CarRentals.com. In her role, she also led the global diversity & inclusion strategies. Now, Sarah is the Chief People Officer at Osler Diagnostics, a health technology company developing innovative biosensor technology as well as being an active angel investor.
Bullpen Capital VC Paul Martino: Fundraising, Venture Activity, and Deal Terms in an Economic Crisis
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During our recent Dreamit Kickoff week, Bullpen Capital Founder and General Partner Paul Martino spoke with our Spring 2020 cohort about the state of the VC ecosystem in the current economic crisis. Martino founded Bullpen in 2010 with a focus on post-seed, pre-Series A startups, and he led the fund’s investments in companies like FanDuel, Namely, Ipsy, SpotHero, Classy, and Airmap. 
Jason Calacanis: Fundraising During the COVID-19 Economic Crisis
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Jason Calacanis (@jason) is a technology entrepreneur, angel investor, and the host of the popular podcasts This Week in Startups and Angel. As a “scout” for top Silicon Valley venture capital firm Sequoia Capital and later as an angel investor, Jason has invested in 200+ early-stage startups including 7 "unicorns" (billion-dollar valuations), including Uber, Thumbtack, Wealthfront, Robinhood, and Calm. 
The CARES Act, PPP Loans, & Startups: Important Updates For Founders
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Friday, April 3 was supposed to be the orderly launch of the CARES Act Paycheck Protection Program (PPP) providing $349B of urgently needed funding to struggling startups and small businesses. Last Friday was anything but orderly. Our three special guests, a leading banker, attorney, and investor, are all on the front lines helping startups to secure emergency funding. Jim Marshall from Silicon Valley Bank (SVB), Kathryn Hickey from PilieroMazza, and Duncan Davidson from Bullpen Capital share the most up-to-date information and what founders need to know and do to get the assistance outlined in the CARES Act.
Geoffrey Moore: Sales Strategies That Work In An Economic Downturn, Provocation-Based Selling
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Acclaimed author and thought leader, Geoffrey Moore (“Crossing the Chasm,” “Inside the Tornado,” “In a Downturn, Provoke Your Customers,” and more) will join us to discuss what companies must do to “provoke” sales during difficult times. During an economic downturn, it’s critical to persuade your customers that your product is not just nice-to-have but an essential tool for their businesses to survive. Provocation-based selling goes far beyond consultative or solution-selling and differs from product-based selling, which pushes features, functionality, and benefits. Provocation-based selling helps customers see their competitive challenges in a new light that makes addressing specific painful problems unmistakably urgent.  
Bullpen Capital VC Duncan Davidson: What Startups Need to Know About the CARES Act
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The $2 trillion CARES Act set aside $377 billion for small businesses. While startups are doing everything they can to extend their runway, there is confusion on if and how the CARES Act applies to startups and what startups need to do to access this funding as quickly as possible. In this #DreamitLive, we discuss:
Marketing & Sales Strategies for Real Estate Tech Startups with Michael Beckerman
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Urbantech Managing Director Andrew Ackerman speaks with CREtech CEO Michael Beckerman about the latest trends in innovation in the commercial real estate industry. Michael Beckerman runs CREtech, the largest event, data and content platform in the commercial real estate tech sector. This position gives him an unparalleled vantage point on emerging tech trends, which technologies are having the biggest impact, and how leading organizations are adapting their companies to integrate technology.
Selling A Cybersecurity Product, Pitch Deck Strategies, & More With Ron Gula
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Ron Gula, president of Gula Tech Ventures, joins Steve Barsh to talk about the 5 most common mistakes cyber entrepreneurs make and how to avoid them. Ron was co-founder and CEO of Tenable where he grew revenue to $100m, customers to 20k, and raised $300m in venture capital. He has invested in dozens of cyber start-ups and supported multiple cyber funds. In this podcast, they discuss the top mistakes Ron and many other prominent cyber investors see cyber startups making and what these startups need to focus on to not only get investment but to build a market-dominating company.
Why Are Unicorns Failing? What Does This Mean for Early-Stage Startups?
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Dreamit’s Steve Barsh speaks with Gil Beyda, Managing Director at Comcast Ventures and Founder & Managing Partner at Genacast Ventures. Steve and Gil dive into why pre-IPO unicorn startups are failing and post IPO valuations are dropping. In addition, based on new market realities, they explore important advice for earlier-stage startup founders on fundraising strategy, valuation, and the key metrics they should pay close attention to.
The Path to Commercialization for a Healthtech Startup
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Dreamit Healthtech Managing Director Adam Dakin speaks with Graftworx founder and CEO David Kuraguntla about his startup’s path to commercialization. Graftworx is a healthtech startup innovating the way remote patient monitoring is done, particularly for those with chronic conditions. By giving clinicians more data on patients, doctors can spot problems earlier and improve patient care.
Building a Brand That Drives Loyalty & Understanding Your Customer
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Powerful brands don't happen by accident. They are the result of deliberate company action most startups are not aware of. Startups often have the vision of being the next Uber, Airbnb, Nike, Apple, Harley Davidson, or the NFL -- powerful brands that have strong customer loyalty. Further, using or being part of the brand becomes part of a customer's social status. In this episode of #DreamitLive, we speak with Dr. Americus Reed II, a leading marketing professor and practitioner at The Wharton School. Americus focuses on studying, building, and nurturing some of the most powerful brands in the world.
How Brex Raised $580 Million in 3 Years
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In the last 3 years, Brex has raised nearly $600 million in venture funding. In this #DreamitLive episode, Michael B. Tannenbaum, CFO & CBO of Brex, and Steve Barsh discuss Michael’s experiences at Brex in raising successive large venture rounds while executing and growing a company quickly. Michael also speaks about his experiences growing SoFi, another fintech unicorn where he was an early executive. We discuss Michael’s top 3 lessons learned and his biggest "Wow, I wish someone had told me that beforehand!" thoughts.
Real Estate Tech Investing, Sales Strategies, & Fundraising Advice with Jeffrey Berman from Camber Creek
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Urbantech Managing Director Andrew Ackerman (@andrewackerman) speaks with Camber Creek General Partner Jeffrey Berman (@Camber_Creek) about all things real estate tech. 
How To Leverage Investor Biases When Raising Capital
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Laura Huang (@LauraHuangLA) is a professor at Harvard Business School and the author of Edge: Turning Adversity into Advantage. Laura teaches that success is about gaining an edge: that elusive quality that gives you an upper hand and attracts attention and support. For some, this comes naturally. For everyone else, Huang provides a framework for creating it. In startups, that edge becomes critical in the fundraising process. For all the talk about due diligence, digging into the financials, and “de-risking” investments, investors often make investment decisions based on “gut feel” and certain biases. For founders, the question is how can you gain an edge by knowing these biases and using them to your advantage.
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