Ben Gilbert and David Rosenthal of Acquired - Lessons on Early Stage Investing and Getting Acquired - [Invest Like the Best, EP.196]
52 min

My guests today are Ben Gilbert and David Rosenthal. Ben and David are investors but also the duo behind the Acquired podcast, which is one of my favorite podcasts that dives deep into business history and famous acquisitions. I recommend you check it out.

In this conversation, we review of some of the greatest corporate acquisitions of all time and also discuss investing lessons Ben and David have learned across their careers. I hope you enjoy my conversation with Ben and David.


This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. 

Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at


This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions.

 With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee.

Learn more and try Assure for yourself at


For more episodes go to

Sign up for the book club and new email newsletter called “Inside the Episode” at

Follow Patrick on Twitter at @patrick_oshag


Show Notes

(2:29) – (First question) – What they look for in new founders based on more experienced managers they’ve worked with

(5:07) – Difference between emerging vs legacy market

(9:17) – Research steps to determine if a market can get big enough to invest in

(12:08) – Working with other firms for doing an initial investment round

(15:42) – Recent trends in the supply of capital and number of founders in the VC space

(18:56) – Lessons they have learned studying corporate transactions

(24:13) – How do startups transform once they are acquired to increase their multiples so much

(28:10) – What they learned from deliberations that take place within the acquiring company

(30:39) – Most interesting deal for them to unpack

(32:44) – What are features of a business that is difficult for others to replicate

(35:52) – Any company that are intimidated to go up against

(37:37) – Who would they follow

            (38:52) – Blake Robbins Podcast Episode

(39:09) – Missing pieces in their skill set

(41:43) – Early green shoots

(44:40) – Lessons from Alaska Airlines acquisition and the value of scarcity

(47:07) – Kindest thing anyone has done for them


Learn More

For more episodes go to

Sign up for the book club and new email newsletter called “Inside the Episode” at

Follow Patrick on Twitter at @patrick_oshag


The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch
Harry Stebbings
20VC: Benchmark's Sarah Tavel on Why Chasing GMV Will Lead To The Wrong Direction, The 2 Crucial Tipping Points For Marketplace Adoption, Why UGC Plays Are Like Marketplaces & How To Determine Between Existential and Non-Existential Risk
Sarah Tavel is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many more. As for Sarah, prior to joining Benchmark, she was a General Partner at another globally renowned firm, Greylock, where she led deals in Sonder and Gixo. Pre-Greylock, Sarah was the first PM @ Pinterest where she led three acquisitions, launched Pinterest internationally, and was responsible for closing their $100m Series C financing. 20VC: Benchmark's Sarah Tavel on Why Chasing GMV Will Lead To The Wrong Direction, The 2 Crucial Tipping Points For Marketplace Adoption, Why UGC Plays Are Like Marketplaces & How To Determine Between Existential and Non-Existential Risk In Today’s Episode You Will Learn: 1.) How Sarah made her way from being the first PM at Pinterest to being a General Partner at one of the world's leading venture firms, Benchmark? 2.) What does Sarah mean when she says, "the small things are not the big things"? How does Sarah determine between existential vs non-existential risk? How does this impact the type of board member Sarah is? How has Sarah seen the best board members engage? Who are they? 3.) Why does Sarah believe that in marketplaces, chasing GMV will lead you in the wrong direction? How does Sarah think about good vs great when it comes to 1.) Average order values? 2.) Repeat purchase rates. 3.) NPS? 4.) Net revenue retention? How should they change with time? 4.) In marketplaces, what is a tipping point? What are the 2 crucial tipping points to be aware of? How can marketplaces ensure demand brings further demand? What can they determine from how demand engages with different suppliers? How does Sarah feel about feedback systems? 5.) Why does Sarah believe that UGC plays are like marketplaces? What lessons can be drawn from TikTok to suggest this? How does Sarah think about her biggest lessons when analysing the growth of DoorDash? What do many not see that is important to recognise? Item’s Mentioned In Today’s Episode Sarah’s Favourite Book: Pachinko: The New York Times Bestseller As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
37 min
Equity Dive: Edtech’s 2020 wakeup call
Hello and welcome back to Equity, TechCrunch’s venture capital-focused podcast (now on Twitter!), where we unpack the numbers behind the headlines. This week, we're doing a first-ever for the show and taking a deep dive into one specific sector: Edtech. Natasha Mascarenhas has covered education technology since Stanford first closed down classes in the wake of the coronavirus pandemic. In the wake of the historic shuttering of much of the United States' traditional institutions of education, the sector has formed new unicorns, attracted record-breaking venture capital totals, and most of all, enjoyed time in a long-overdue spotlight. For this Equity Dive, we zero into one part of that conversation: Edtech's impact on higher education. We brought together Udacity co-founder and Kitty Hawk CEO Sebastian Thrun, Eschaton founder and college drop-out Ian Dilick, and Cowboy Ventures investor Jomayra Herrera to answer our biggest questions. Here's what we got into: * How the state of remote school is leading to gap years among students * A framework for how to think of higher education's main three products (including which is most defensible over time) * What learnings we can take from this COVID-19 experiment on remote schooling to apply to the future * Why ed-tech is flocking to the notion of life-long learning * And the reality of who self-paced learning serves -- and who it leaves out And much, much more. If you celebrate, thank you for spending part of your Thanksgiving with the Equity crew. We're so thankful to have this platform and audience, and it means a ton that y'all tune in each week. Finally, if you liked this format and want to see more, feel free to tweet us your thoughts or leave us a review on Apple Podcasts. Talk soon!
26 min
North Star Podcast
North Star Podcast
David Perell
Nik Sharma: Building DTC Companies
My guest today is Nik Sharma, the founder of Sharma Brands and an advisor to companies like Judy and Cha Cha Matcha. Nik is one of my very best friends and my go-to person for all things commerce. Since we first met, we've spent hours exploring the future of marketing and commerce together and recorded this podcast to give you a window into what our conversations are like. We started with Nik's philosophy of launching Direct-to-Consumer brands. I particularly liked Nik's idea of "The Brag Bar" on landing pages, where you can use social proof to sell your products. We also spoke about managing relationships with influencers and finding the supply and demand equilibrium at launch. Towards the end, Nik and I talked about our process for turning conversations into articles, and the time he cold emailed Mark Cuban. Please enjoy my conversation with Nik Sharma. ____________________________ Show Notes 2:21 - Why Nik has the "world's craziest fridge" and how it helps keep him in the know on DTC brands. 6:29 - What marketing strategies Nik has found most successful for DTC brands. 13:31 - How brands can differentiate themselves in a world of emerging brands in already burgeoning markets. 19:25 - Nik's approach to launching a successful DTC brand and when to concentrate your advertising versus diversify. 30:19 - The role of A/B testing in building a brand. 35:43 - How influencers play into the big picture of marketing and why the "shaky video" effect is so successful. 42:12 - The selection and audition process of influencers in Nik's campaigns and how he chooses those he sees as the best for his brands. 45:52 - The costs and benefits of starting your brand through heavy promotion via influencers. 49:56 - How the process of rebranding Hint Water's bottle was performed and the qualitative process that got them to the bottle you see today. 57:27 - The metrics and methods Nik uses in his development of marketing strategies with his brands. 1:05:19 - What Nik looks for in a great landing page, and why all landing pages should be easy to read for everybody from a 12-year-old to a drunk person. 1:10:07 - What UGC is and why Nik thinks it is so underrated by marketing teams. 1:13:31 - The different marketing funnels and when you should use each one. 1:17:09 - Why Nik creates landing pages for fake products and makes them live on the internet. 1:22:56 - The importance of having great merch for your brand. 1:26:22 - What about internet culture makes collaborations so successful and popular. 1:34:05 - How somebody can convert a large personal following into sponsorships and meaningful collaborations. 1:35:46 - How new brands should position themselves when huge players like Amazon are in the same space. 1:44:01 - What happened when Nik cold emailed Mark Cuban and how he got an almost instant response. 1:50:46 - How David and Nik collaborate to develop, write, and publish the articles they make. 1:56:14 - Why Nik doesn't sweat the details of his personal brand that much.
2 hr 1 min
The Acquirers Podcast
The Acquirers Podcast
Tobias Carlisle
Value: After Hours S02 E46 Buffett sells $COST, Einhorn's $GLRE and Icahn's $IEP, Long-lived Instos
Value: After Hours is a podcast about value investing, Fintwit, and all things finance and investment by investors Tobias Carlisle, Bill Brewster and Jake Taylor. See our latest episodes at  Jake's Golden Jubilee offer: Donate to the FinTwit Value vs Growth War here (it's for a good cause--The American Foundation for Suicide Prevention): About Jake: Jake is a partner at Farnam Street. Jake's website: Jake's podcast: Jake's Twitter: Jake's book: The Rebel Allocator About Bill: Bill runs Sullimar Capital Group, a family investment firm. Bill's website: Bill's Twitter: @BillBrewsterSCG ABOUT THE PODCAST Hi, I'm Tobias Carlisle. I launched The Acquirers Podcast to discuss the process of finding undervalued stocks, deep value investing, hedge funds, activism, buyouts, and special situations. We uncover the tactics and strategies for finding good investments, managing risk, dealing with bad luck, and maximizing success. SEE LATEST EPISODES SEE OUR FREE DEEP VALUE STOCK SCREENER FOLLOW TOBIAS Website: Firm: Twitter: LinkedIn: Facebook: Instagram: ABOUT TOBIAS CARLISLE Tobias Carlisle is the founder of The Acquirer’s Multiple®, and Acquirers Funds®. He is best known as the author of the #1 new release in Amazon’s Business and Finance The Acquirer’s Multiple: How the Billionaire Contrarians of Deep Value Beat the Market, the Amazon best-sellers Deep Value: Why Activists Investors and Other Contrarians Battle for Control of Losing Corporations (2014) (, Quantitative Value: A Practitioner’s Guide to Automating Intelligent Investment and Eliminating Behavioral Errors (2012) (, and Concentrated Investing: Strategies of the World’s Greatest Concentrated Value Investors (2016) ( He has extensive experience in investment management, business valuation, public company corporate governance, and corporate law. Prior to founding the forerunner to Acquirers Funds in 2010, Tobias was an analyst at an activist hedge fund, general counsel of a company listed on the Australian Stock Exchange, and a corporate advisory lawyer. As a lawyer specializing in mergers and acquisitions he has advised on transactions across a variety of industries in the United States, the United Kingdom, China, Australia, Singapore, Bermuda, Papua New Guinea, New Zealand, and Guam.
1 hr 3 min
Ben Gilbert and David Rosenthal
Virgin Galactic
Live from the 2020 ASCEND Space Conference, Acquired covers the full story behind the most "out there" technology story of the past few years: Virgin Galactic. How did this space tourism company grow out of the winning X Prize team, and catch the eyes and fancy of billionaires like Paul Allen, Sir Richard Branson, and, most recently, company chairman Chamath Palihapitiya who took it public via the first "modern" technology SPAC transaction in history? Tune in to find out!! If you want more more Acquired and the tools + resources to become the best founder, operator or investor you can be, join our LP Program for access to our LP Show, the LP community on Slack and Zoom, and our live Book Club discussions with top authors. Join here at: Sponsors: * Thanks to Tiny for being our presenting sponsor for all of Acquired Season 7. Tiny is building the "Berkshire Hathaway of the internet" — if you own a wonderful internet business that you want to sell, or know someone who does, you should get in touch with them. Unlike traditional buyers, they commit to quick, simple diligence, a 30-day or less process, and will leave your business to do its thing for the long term. You can learn more about Tiny here: * Thank you as well to Bamboo Growth and to Perkins Coie. You can learn more about them at: * * Playbook Themes from this Episode: (also available on our website at ) 1. Prizes can be a great way to generate leverage on innovation. If done right, the X Prize and other industry prizes like it (e.g., Netflix Prize, DARPA Challenge, etc) can bring an order of magnitude more talent to bear on a challenge than what the same dollars alone could hire. * The challenge is to create a prize that inspires and draws in a large enough pool of contributors. The aerospace industry’s “cool” factor may be what allowed the X Prize to succeed and explain why prizes aren't employed as often in other sectors. 2. When trying new things, most people want to go second — but those willing to go first get the best returns.Being first into new markets carries high risk (including/especially reputational), but often also offers asymmetric upside. Investing in a new frontier when others think it’s crazy is a recipe for success — if you’re both contrarian and right. * Chamath took a huge turn from the traditional VC playbook when he created his first SPAC in 2017, years before they went mainstream. He and his investors have generated over $1B in profits from that vehicle (which is now merged with Virgin Galactic), and have since used those proceeds to launch five more. 3. The best time to invest was yesterday, the next best time is today. Great investors don’t miss the chance to invest in big markets because they’ve passed on it before. Sir Richard Branson passed on investing in the X Prize twice before partnering with Burt Rutan's winning team to build Virgin Galactic. 4. Whenever a market's prices aren't being set by supply and demand, there's probably an opportunity to disrupt that market. The traditional IPO pricing process is managed by third parties (investment banks) that represent both sides of the transaction, and also have their own economic interests at play. It's the equivalent of a real estate agent representing both the buyer and seller. As a result, many technology IPOs have left hundreds of millions or billions of dollars on the table. SPACs and direct listings are now solving that problem. Any other market with this dynamic should represent fertile ground for entrepreneurs. Links: * Virgin Galactic's "One Small Step" reservation program: * The November 2020 launch delay: Sources: * Black Sky Documentary: * How to Make a Spaceship: * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *
1 hr 45 min
All-In with Chamath, Jason, Sacks & Friedberg
All-In with Chamath, Jason, Sacks & Friedberg
Jason Calacanis
E13: SPACsgiving Special! More promising vaccine news, innovation vs. regulation, reforming higher ed, morality of challenge trials & more
Follow the crew: Follow the pod: Referenced in the show: NYT Article - Politics, Science and the Remarkable Race for a Coronavirus Vaccine Show Notes: 0:00 Besties congratulate Friedberg & Chamath for taking Metromile public, Chamath explains a PIPE, Sacks & Jason express their discontent for being left out of the first bestie SPAC 10:59 More positive vaccine news, NYT article on Operation Warp Speed: did the Trump administration nail it? 21:50 How will the COVID experience impact the response to the next pandemic? Morality of challenge trials, hypocrisy of regulatory capture around gambling, drug use, pharma, etc. 35:25 Why innovation has occurred so rapidly on the Internet: Permissionless innovation & lack of regulators, regulation vs. innovation 47:07 Thoughts on ISAs & how they could disrupt overpriced higher education, Dave Chappelle's contract with Comedy Central 59:58 Trump accepts defeat (sort of), Biden's cabinet selections so far 1:06:29 What the besties are thankful for 1:14:50 Peace in the Middle East being achieved by declining reliance on oil, based on resume alone - would Trump have won if not for his antics? 1:21:01 Code 13!
1 hr 22 min
16 Minutes News by a16z
16 Minutes News by a16z
Andreessen Horowitz
Transparency in Pricing, Ruling Healthcare
[simplecast-embed src=""] The Centers for Medicare & Medicaid Services (CMS) issued the latest in a series of “historic" rules a few weeks ago; the controversial rules -- which have been in the works for a while, but are now final -- are intended to increase price transparency in (what's been described by the U.S. Department of Health and Human Services’ secretary as) a "shadowy system where prices are hidden". Specifically, the two rules will require hospitals, group health plans, and health insurance issuers to disclose _price_ and _cost-sharing_ information to participants, beneficiaries, and enrollees _up front_; give patients _accurate_ estimates of the costs that they are responsible for, including making previously unavailable price information _accessible_ to them and other stakeholders; and doing so in a _standardized_, _machine-readable_ way that allows for easy comparisons (and therefore more choice and competition). So in this episode of 16 Minutes, a16z bio experts Justin Larkin and general partner Julie Yoo (who also interviewed Dr. Marty Makary, author of _The Price We Pay_, on a previous episode) join Sonal Chokshi to discuss the specifics of, and the impact of, the rules on consumers and on various industry players. As is the premise of the show, they also break down the gap between what's hype/ what's real when it comes to mandates and implementation; while the rules go into effect January 2021, the deadlines roll out through 2024. What are the tensions (and paradoxes!) between hospitals and insurers, between efficient markets and top-down policy, between price vs. cost, between planned vs. surprise costs, between shoppable and non-shoppable services, between price and quality, price and value? Where do incentives align (or not)? And what are the challenges, and opportunities, for builders?
23 min
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