The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman.
If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.
20 Sales: Three Reasons Why Sales People Fail | The Two Things That Matter When Hiring Sales Leaders | Why Revenue, Discounting and Price Do Not Matter in the Early Days with Jordan Van Horn, Revenue Leader @ Monte Carlo
Jordan Van Horn is a Revenue Leader @ Monte Carlo, the world's first data observability company. Prior to this role, Jordan spent an incredible 4 years in sales at Segment including as VP of Sales leading a sales team of 50+ Account Executives and leading the first international expansion for the company into Dublin. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business in California.
In Today's Episode with Jordan Van Horn We Discuss:
1.) Entry into the World of Sales:
How did Jordan make his way into the world of sales first with a vineyard? What are 1-2 of the biggest takeaways for Jordan from seeing the scaling sales teams at both Segment and Dropbox? How did seeing that impact his mindset? What does Jordan know now that he wishes he had known when he entered sales?
2.) The Sales Playbook:
How does Jordan define "the sales playbook"? What is it not? What five core things should the sales playbook help you accomplish? Should the founder be responsible for the sales playbook? Can it be created by a Head of Sales? How does Jordan advise founders on three signals that now is the right time to bring in a sales hire? How does Jordan advise founders on whether the first sales hire should be a rep or a leader?
3.) The Secrets to Pricing and Discounting:
Why does Jordan not care what price customers pay in the early days? If it is not about ARR, what should teams be optimizing for? When does price discipline become important in a company journey? What are the dangers of not having price discipline? What two tools do sales leaders have to use in order to create urgency in a deal closing process? How should sales leaders think about building multiple champions within a potential customer? At what price point is it worth it?
4.) The Hiring Process:
How does Jordan structure the hiring process for all new sales hires? What are the must-ask questions that Jordan asks all new candidates? What does he want to see in those answers? Who else does he bring into the hiring process? At what stage do they get involved? What are they testing for? Does Jordan use case studies with candidates? What makes the best? What makes the worst?
5.) The Onboarding:
What is the ideal onboarding process for new sales reps? What should founders do and prep for when onboarding their first sales hires? What materials and recordings should they have ready? What are some early signs that a new hire is not working out? How do we measure their impact? For enterprise sales, it takes a long time to close new deals, how can one determine effectiveness of new reps when the sales cycle is so long?
20VC: Fintech OG Sheel Mohnot on Lessons from Investing in Flexport and ChipperCash and Missing Robinhood and Chime, Why Overly Large GP Commits are Dangerous, Biggest Mistakes Managers Make with Fund I and Emerging Markets; Which Survive?
Sheel Mohnot is a Co-Founder and General Partner @ Better Tomorrow Ventures, a $225M fund that leads rounds in pre-seed and seed-stage fintech companies globally. Sheel and Jake (his co-founder) invested for many years together before founding BTV and wrote checks into Mercury, Flexport, Ramp, and Hippo Insurance to name a few. As for Sheel, before BTV he ran 500 Fintech for close to 7 years, and before that was a founder, founding two companies, both of which were acquired. If that was not enough, Sheel is also a master at measuring the width of swimming pools and making cameo appearances in music videos with Justin Bieber.
In Todays Episode with Sheel Mohnot We Discuss:
1.) Entry into Venture:
How Sheel made his way into the world of venture having founded 2 fintech companies? Why did no LPs give Sheel money in the early 500 Fintech days? What were some of his biggest lessons from investing in 100s of companies with 500 Fintech? How did BTV with Jake come together most recently? What are the biggest differences to Sheel of being a fund manager vs being an investor?
2.) The Power Law:
How does Sheel define "the power law" in venture capital? What multiple of return would be power law status? Given the size of outcome available with these power law returns, how does Sheel approach portfolio construction? Would it not be best to invest in 100s of companies? Who does Sheel believe has done the indexing approach best? Why?
3.) Venture Capital has Never Been Less Collaborative:
Why does Sheel disagree with Harry that venture capital has never been less collaborative? Why now, for the first time, are large multi-stage funds taking single-digit ownership? Does Sheel agree with Harry it is moronic to have "guaranteed pro-rata"? How does Sheel approach re-investment decision-making? When does he pay up vs not?
4.) The Biggest Wins and Misses:
What have been Sheel's biggest wins from a cashback and a multiple perspective? How did Sheel miss the chance to invest in both Robinhood and Chime early on? What did he not see? How would he have thought differently with the benefit of hindsight? How have Sheel's biggest hits and misses impacted how he invests today?
5.) Emerging and Frontier Markets:
Does Sheel share Harry's concern for the removal of capital from emerging markets? Why does Sheel believe that India, South East Asia and LATAM will be fine? Why does Sheel believe Pakistan and Africa are most in trouble? What advice does Sheel give to his emerging markets founders today?
Items Mentioned in Today's Episode:
Sheel's Favourite Book: Enders Game
20VC: 13 of the Great Investing Minds on When to Pay Up vs When To Remain Disciplined and Walk Because the Price is too High: The Ultimate Guide to Price Sensitivity
Marcelo Claure is an entrepreneur and investor who has founded and led some of the world’s most iconic businesses. He is currently the Chairman & CEO of Claure Capital, a newly founded multi-billion-dollar global investment firm. Before this, Marcelo was COO @ Softbank Group, the world’s largest technology investment company.
Bill Gurley is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including Uber, Twitter, Dropbox, Modern Treasury, Snapchat, StitchFix, and many more.
Michael Eisenberg spent 15 years as a General Partner @ Benchmark working alongside Bill and the Benchmark partnership. Following Benchmark, Michael co-founded Aleph, one of the leading Israeli venture funds of the last decade.
David Tisch is the Founder and Managing Partner @ Box Group, one of the leading seed focused firms of the last decade with a portfolio including Airtable, Glossier, PillPack, Plaid and many more.
Cyan Banister is one of the most successful and renowned early-stage investors in the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few.
Zach Weinberg is a Co-Founder of Operator Partners, operators funding operators, with no outside LPs, just their own capital.
Luciana Lixandru is a Partner @ Sequoia, one of the world’s most renowned and successful venture firms with Sequoia-backed companies accounting for more than 20% of NASDAQ’s total value.
Jeff Lieberman is the Managing Director @ Insight Partners, one of the leading investing franchises of the last 25 years with their most recent flagship fund announced earlier this year being a staggering $20BN.
Nick Shalek is a General Partner @ Ribbit Capital, specializing in fintech they are one of the most successful venture firms of the last decade with a portfolio including Robinhood, Coinbase, Revolut, Nubank and more.
Frank Rotman is a founding partner of QED Investors, one of the leading fintech-focused venture firms investing today with a portfolio including the likes of Klarna, Kavak, Quinto Andar, Credit Karma and more.
Geoff Lewis is the Founder and Managing Partner @ Bedrock, now with over $1BN in AUM, Bedrock invests in breakout technology companies that are incongruent with popular narratives.
Justin Fishner-Wolfson is founder and the managing partner of 137 Ventures. Their portfolio includes SpaceX, Wish, Anduril, Flexport, and WorkRise (formerly Rigup) to name a few.
David Sze is a General Partner @ Greylock where he has led some of the firms most notable investments including Facebook, LinkedIn and Pandora.
In Today's Episode We Discuss Price Sensitivity:
1.) How do you assess your relationship to price and price sensitivity?
2.) When is the time to pay up and have less price discipline?
3.) When should we remain disciplined and not pay up for a deal and walk away because of price?
4.) Of the deals you have paid up for, did their growth rate justify the high entry price?
5.) Knowing all you know now on price, how do you advise younger investors today?
20 Growth: Why You Need a Growth Hire Pre Product-Market-Fit? Why Every Company Will Be a Media Company and How To Do It | Communities; What Really Are They? How To Build Them? What Makes The Best? Why Do Many Not Work? | Kieran Flanagan, SVP Marketing
Kieran Flanagan is SVP Marketing at HubSpot, where he has helped the business grow internationally, move to a product-led business, quadrupled its marketing demand, and built out its media team, including the acquisition of 'The Hustle.' He is also an advisor and investor in early-stage companies.
In Today's Episode with Kieran Flanagan We Discuss:
1.) Entry into Growth and Marketing:
How did Kieran make his way into the world of growth and marketing? What has been 1-2 of Kieran's biggest lessons from seeing firsthand the hyper-scaling of Hubspot? On reflection, how would Kieran summarise both Hubspot's community building attempts and also their product messaging?
2.) Why You Need Growth Hires Pre Product Market Fit:
What does "growth" mean to Kieran? Where do so many get it wrong? Why does Kieran believe that you should have a growth team/people before product market fit? What specifically do they do and work on during this stage? Pre PMF, what is the core metric that all startups should focus on? How does it change with time?
3.) Building Your Growth Team:
What does Kieran believe are the 3 key stages to hiring for growth? How should founders determine whether to have external standalone growth teams or integrate them into existing functions? What are the single biggest mistakes founders make when hiring for growth?
4.) The Future is Content:
Why does Kieran believe every great tech brand will have to become a media brand? Why is Elon Musk an example of the perfect brand? What has he done right? Why does Kieran say that data is the best and worst thing that has happened to marketing?
5.) WTF Really is Community:
How does Kieran define "community"? What is it? What is it not? What makes the best communities? Why do some work and others not? Should every company have a community approach? Who does it make sense for? Have Hubspot done a good job at community building? On reflection, is there anything that Kieran would have done differently?
20VC: Investing Lessons from Fred Wilson and Why Small Funds Outperform Large Funds | Why the Secret to Winning in Venture is Splitting Deals |Learnings From the Biggest Hits and Biggest Losses | Why Anyone That Always Does Their Pro-Rata is Wrong with
Mo Koyfman is the Founder and General Partner @ Shine Capital, who announced earlier this year Shine II, a $200M early-stage fund, and Shine Opportunities I, a $100M vehicle. Prior to founding Shine, Mo was the Managing Member @ Moko Brands where he made angel investments in Coinbase, Polychain, Harry's to name a few. Before Moko, Mo spent over 7 years as a General Partner @ Spark Capital where he made investments in Plaid, Warby Parker, Skillshare and Hivemapper, to name a few. Finally prior to Spark, Mo spent over 5 years at IAC where he oversaw group of companies that included Connected Ventures, parent of Vimeo, CollegeHumor & BustedTees.
In Today's Episode with Mo Koyfman:
1.) From Entrepreneurial Parents to IAC, Spark Capital and Founding Shine:
How did Mo make his way into the world of venture having worked with Dara Khros, Barry Diller and Jeremy Liew? What were some of the biggest takeaways from his time with Barry Diller and IAC? How did Mo's time at Spark impact his investing mindset? What did he learn that he took with him to founding Shine?
2.) Investment Firm vs Investment Partnership:
What are the biggest differences between investment firms and investment partnerships? What are the biggest risks founders are taking when they take money from investment firms? Mo has very strong beliefs, how does he manage and inspire debates within his firm without shutting down or intimidating younger, less experienced team members? What does Mo mean when he says, "firms are great but partners matter".
3.) How To Win in Venture:
Why does Mo always believe that small funds outperform large funds? What have been some of Mo's biggest lessons from Fred Wilson on fund strategy and sizing? How much of an emphasis does Mo place on the importance of ownership? Why does Mo believe the way to win in venture is to be collaborative? Why does Mo believe in the macro conditions we are entering, the landscape is about to become a lot more collaborative? Why does Mo believe any firm that says they will always do their pro rata is lying?
4.) The Lessons: Success and Failure:
What are some of Mo's biggest lessons from his biggest wins, like Plaid at seed? That said, why does Mo believe it is so dangerous to try and learn lessons from the wins? What failures have been most impactful to Mo? What did he take away from them? Why does Mo believe that making great burgers is like building great companies?
Items Mentioned in Today's Episode:
Mo's Favourite Book: Portnoy's Complaint by Philip Roth
20VC: Raising $60M and Not Touching a Dollar of It; The 3 Decisions That Led to a Cash-Flow Positive Business, Why Not Being Able To Fundraise in the Early Days Can Help Build Your Business & What are the First Things To Break in Scaling Orgs with Samee
Sameer Shariff is the Co-Founder and CEO @ Cambly, the company that allows you to become fluent faster through one-on-one video chat lessons with native English tutors. To date, Sameer has raised over $60M with Cambly from the best including Jeremy Levine @ Bessemer, Sarah Tavel @ Benchmark, Monashees, YC and more. Prior to founding Cambly, Sameer spent close to 5 years at Google on the Search Quality team and became the Tech Lead of the Search experiments team helping make experimentation a core part of the launch process.
In Today's Episode with Sameer Sharif We Discuss:
1.) Entry into Startups and Co-Founding Cambly:
How did Sameer make his way into the world of tech with his joining Google straight out of college? What were the 1-2 biggest takeaways from his time at Google? How did it shape his mindset? What was the a-ha moment for Sameer with Cambly?
2.) The Trials and Tribulations of Leadership:
What does "high performance" mean to Sameer in business? How has it changed over time? What are the first things to break in a scaling company? How do the best companies retain speed and agility with scale? What are the single biggest hiring mistakes Sameer has made? What did he learn?
3.) The Fundraise that Led to Cash Flow Positive:
Why does Sameer think it was so hard to fundraise for Cambly in the early days? When they failed to raise their Series A, what 3-4 core decisions did they make to get Cambly to cash flow positive as fast as possible? How did Sameer communicate their failed fundraising to the team? How did he do this in a way that rallied the troops and did not worry or scare them? What was the tipping point for fundraising to become much much easier for the company? Given they have not touched any of their Series A or Series B funds, how does Sameer think about the balance of growth vs profitability?
4.) Marketplace Dynamics 101:
How did Cambly acquire the first 100 customers on the demand side? What is the most challenging dynamic of Cambly; demand or supply side? Where does Sameer see most marketplace founders make the biggest mistakes? What does Sameer know now on the intricacies of marketplace dynamics that he wishes he had known at the beginning?
Items Mentioned In Today's Episode with Sameer Shariff:
Sameer's Favourite Book: The Most Human Human: What Artificial Intelligence Teaches Us about Being Alive