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34 minutes
Randy Glein is a Co-Founder & Partner @ DFJ Growth where he looks to partner with entrepreneurs that have achieved market validation and are looking to scale rapidly. Randy's investments include the likes of Twitter, Tumblr, SpaceX and Tesla just to name a few. Prior to DFJ, Randy was CFO @ Feedburner (acq by Google), a business development executive at DIRECTV. Randy was also named to the Forbes Midas List in 2013, 2014, and 2015 as one of the world's top tech investors and to the New York Times / CB Insights list of top 100 venture capital investors in 2016. In Today’s Episode You Will Learn: 1.) How Randy made his way into VC and came to found DFJ growth? 2.) What does it mean to be a diligent and disciplined investor? How can a futuristic mindset be balanced with an analytical and academic approach to evaluation and due diligence? 3.) How does Randy evaluate invest time horizons? How important is it to push for liquidity events as soon as possible? What is it that LPs really want to see? 4.) How have we seen public market expectations of tech companies change over the last 10 years? What are public market investors willing to give up in exchange for predictability? What are the benefits of tech companies staying private longer? 5.) What are the metrics that suggest a company with market validation and ready to scale into hyper-growth? What are the required levels of revenue and ARR? Items Mentioned In Today’s Show: Randy’s Fave Book: Being Digital Randy's Fave Blog: Brad Feld, Fred Wilson Randy’s Most Recent Investment: Unity 3D As always you can follow Harry, The Twenty Minute VC and Randy on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to and also at  
7 minutes
The amount of venture capital investment in Chicago startups is on the rise. Or maybe not. Depending on how you crunch the data, the first quarter of this year was either lackluster or spectacular. Regardless of how the numbers break down, hundreds of millions of dollars in venture capital are flowing to companies in our city every year. So, where’s all that money going? And what effect is it having? Jason Heltzer is a Chicago-based VC who’s a partner at Origin Ventures. He also teaches at the University of Chicago’s Booth School of Business. He joins us with a venture capitalist’s perspective on the local VC economy.
24 minutes
Krishna Gupta, Founder and General Partner of Romulus Capital, joined Seedcamp in Boston on our recent US Trip. Krishna founded Romulus in 2008 whilst studying at MIT. He formed the fund to plug the gap between angel investments and big funds, creating a firm to help build early-stage businesses. In our interview he discusses his entrepreneurial nature and young career that lead to Romulus and his views on the current state of the Seed stage investment market. He also gives his key advice for foreign companies looking to expand to the US and why more startups should be thinking about longer term business plans when scaling.
13 minutes
Some of Silicon Valley's most successful companies have yet to go public. The private world of "unicorns" is a gentler place than the stockmarket, perhaps artificially
43 minutes
Entrepreneur Jay Kaplan, co-founder and CEO of Synack, describes how the idea of creating a cybersecurity service for enterprise businesses by crowdsourcing hackers went from sounding like a long shot to launching as a venture capital-backed startup. Kaplan, previously a senior analyst at the National Security Administration, talks about the virtues of government work and the nuances of “white hat” hacking.
less than a minute
Chad Boeckmann of Secure Digital Solutions joins us for an interview. In startup news this week, we talk about why many boom-time startups are fizzling out, the average age of startup founders, why Johnson & Johnson is getting into startups, and much more. Stay tuned!
about 1 hour
Ben & David chat with Brian Schultz, the Managing Director of Strategic Investments & Corporate Development at Microsoft, about Microsoft’s approach to M&A, investing, and partnering with startups — and his journey from acquirer to acquiree and back again!  Topics covered include: Brian’s history working across “both sides of the aisle” as both a startup founder and corporate development leader at a big company, how perspective from each informs the other, and the importance of learning “customer empathy”  How Microsoft approaches M&A from an organizational perspective, and the importance of fit with the company’s product roadmap  How Brian approaches strategic investments at Microsoft, and the evolution over time of the Microsoft (and large technology companies as a whole) perspective on investing in other companies Balancing the tension between partnering and investing, and what criteria Brian thinks about when evaluating companies  Microsoft’s investment in Facebook in 2007 (at a then-crazy-seeming $15B valuation), and more recently Foursquare, Mesosphere, CloudFlare and others The current state of the tech M&A landscape, and the emergence of private equity as tech company acquirers  Potentially changing corporate and foreign tax structures and how they impact acquirers’ thinking around deals (or not!)  How Microsoft tracks and evaluates success of acquisitions over time, and lessons learned from successes and failures  The increasing number of operating companies (technology and otherwise) looking to invest in startups, and how that landscape has evolved over time  Followups: Snap Inc.’s rumored IPO filing — and bonus discussion of how VC’s and other investors think about “exiting” their investments in companies that have gone public Hot Takes: Amazon Go! The Carve Out: Ben: OK Go - The One Moment  David: UC Berkeley Oral History with Sequoia Capital founder Don Valentine Brian: Om Malik’s recent piece in the New Yorker: Silicon Valley Has an Empathy Vacuum
about 1 hour
 - A few weeks ago, Dan and Ian mentioned that they would be inviting their friend Dan Norris back onto the program. Dan Norris is the author of The 7 Day Startup, and for lack of a better term, he is a business idea generating machine. There have been success stories on this show that came from many of Dan's business ideas. In this conversation, Dan donates a ton of business ideas, as well as sharing how he has been able to create a six-figure side hustle through self-publishing books. If you are looking for your next entrepreneurial adventure, this could be the episode for you.