The Twenty Minute VC (20VC): Venture Capital | Startup Funding

Latest Episodes:

20VC: PagerDuty CEO Jennifer Tejada on A Leader's Relationship To Risk, Insecurity, Making Decisions with Imperfect Data & What Successful Board Management Looks Like Aug 28, 2020

Show notes

Jennifer Tejada is the CEO @ PagerDuty, the company that provides a real-time operations platform ensuring less downtime for your digital services. Prior to their IPO in 2019 PagerDuty raised funding from some of the best in the business including Accel, a16z, Baseline, Bessemer and Harrison Metal to name a few. As for Jennifer, prior to PagerDuty, she was CEO of Keynote Systems leading to their acquisition by Dynatrace. Before Keynote, Jennifer was Executive Vice President and Chief Strategy Officer at Mincom, leading them to their acquisition by ABB. If that was not enough, Jennifer is also on the The Estée Lauder Companies Inc. (NYSE: EL).

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In Today's Episode You Will Learn:

1.) How Jennifer made her way into the world of SaaS and came to be one of the leading enterprise CEOs today with PagerDuty? How does Jen advise graduates on joining a startup vs large incumbent?

2.) How does Jen analyse and evaluate her relationship to risk? What does Jen do to remove herself from her environment and make the clearest decisions? How has Jen's decision-making process changed? How does Jen encourage debate and free thought sharing internally?

3.) How does Jen think about the role of insecurity within leadership? What would Jen say are her biggest insecurities? How does Jen manage them and mitigate them today? What works? What does not? Why does Jen believe data is the key to overcoming insecurities?

4.) What have been Jen's biggest lessons on what successful board management looks like? What separates good vs great board members? How can CEO's structure their board in an optimal way? What do they need? What do they not need? How does scale change this?

5.) How does Jen think her style of leadership has changed over the years? What have been Jen's lessons on what it takes to both acquire and retain the very best execs? Where do many go wrong here?

Items Mentioned In Today's Show:

Jennifer's Fave Book: Tuesdays With Morrie: An old man, a young man, and life's greatest lesson

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.

20VC: Sahil Lavingia on Rolling Funds and Their Impact on The Future of Venture, How To Evaluate Market, Team and Product, The Value of Party Rounds & The Pros and Cons of Multi-Stage Funds Investing at Seed Aug 24, 2020

Show notes

Sahil Lavingia is the Founder and CEO @ Gumroad, the company that helps creators do more of what they love. With Gumroad, Sahil has raised funding from an all-star list of investors including Accel, Kleiner Perkins, First Round and then Max Levchin, Chris Sacca, Ron Conway and Naval Ravikant on the individual side. However, most recently Sahil has made waves launching one of the first rolling funds on AngelList with his being $6M per year. In the past, Sahil has backed the likes of Lambda School, Figma, HelloSign and Haus to name a few.

In Today's Episode You Will Learn:

1.) How did Sahil make his way into the world of startups and angel investing? What were his biggest takeaways from being employee #2 at Pinterest? How did that experience impact his mindset?

2.) Why did Sahil decide to make his new fund an AngelList rolling fund? How is it structured? Does Sahil think this will represent a seismic shift in early stage investing? Is this a game of the 1%? Why does Sahil think early-stage remains so undervalued? How will this impact Series A pricing?

3.) How does Sahil assess his own price sensitivity today? How does Sahil think about the right way to turn down a founder? Where do many go wrong? How does Sahil feel about the rise of pre-empted rounds? How does Sahil advise seed founders with offers from multi-stage firms?

4.) What does Sahil believe founders care most about today in their investors base? How does Sahil think about investor brand and distribution? How does Sahil analyse the pros and cons of party rounds? How does Sahil advise founders on constructing their early cap table?

5.) How does Sahil think about his relationship to risk and to money? How did Sahil deal with it when his investors wrote off his company? How did Sahil feel about the weight of expectation placed on his shoulders at such a young age? How did he deal with this?

Items Mentioned In Today's Show:

Sahil's Fave Book: How to Win Friends and Influence People

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.

20VC: Biggest Lessons From Scaling Houseparty To Millions of Users, Why Today's Metrics Are Insufficient To Determine Product Success & What Breaks with Scale From Team To Product with Ben Rubin, Co-Founder @ /talk & Houseparty Aug 21, 2020

Show notes

Ben Rubin is the Founder & CEO @ /talk, the anti-meeting tool for fast, decentralised conversations. Prior to co-founding /talk, Ben was the Co-Founder & CEO @ Houseparty, where he scaled the product to millions of users and raised over $70M in funding from the likes of Sequoia, Greylock and Entree Capital to name a few. In addition over the last few years Ben has enjoyed roles at Sequoia as a Scout and then also at Benchmark as an Entrepreneur-In-Residence.

In Today's Episode You Will Learn:

1.) How Ben made his way into the world of startups and came to found Life on Air, later turning into Meerkat and Houseparty?

2.) What were Ben's key learnings from the Houseparty scaling experience? Why are the traditional metrics we use to measure startup success (DAU, MAU etc) insufficient? What is the nuance to metrics? How does Ben think about being first to market vs being the best to market?

3.) How does Ben believe the product principles differ when comparing the 0-1 stage vs 10-100 stage? How does Ben think about where to be rigorous on product? How does Ben advise founders to discover the key guiding product principle? What was it for Ben with Meerkat?

4.) Meerkat pivoted to Houseparty 3 months after having raised $40M, how did Ben communicate that to the board? How did they respond? How does Ben believe the best boards operate? What does Ben most look for in his board members? Where do many go wrong with board management?

5.) From the team side, when in hypergrowth, when do things start to break? What profiles are usually the first to break? Does that mean one should not hire those profiles? What can the leader do to create that intimacy and trust amongst the team?

Items Mentioned In Today's Show:

Ben's Fave Book: Seneca: The Shortness of Life

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.

20VC: Why Entrepreneurs Care Less About Firm Brand at Seed, How LPs Should Think About GP Commit & How The World of LPs and Fundraising Will Change Post COVID with Apurva Mehta, Managing Partner @ Summit Peak Investments Aug 17, 2020

Show notes

Apurva Mehta is the Managing Partner @ Summit Peak Investments, investing in early stage venture capital funds and making direct co-investments. To date they have backed the likes of Raymond Tonsing, Lachy Groom and Josh Buckley to name a few on the fund side and then on the direct side, invested in Airtable, Virta Health and Sourcegraph. Prior to founding Summit Peak, Apurva spent 7 years as the Deputy Chief Investment Officer at Cook's Children's Hospital and before that spent 3 years as Director of Portfolio Investments at The Juilliard School.

In Today's Episode You Will Learn:

1.) How did Apurva make his way into the world of fund investing? How did that lead to his founding Summit Peak and also becoming a GP?

2.) How does Apurva think about how much importance to place on references when diligencing managers? What reference types mean a lot? Which mean less? Why does Apurva still believe early-stage is the most inefficient segment of the venture landscape?

3.) How does Apurva think about GP commits? Is it fair to have a required benchmark? How does Apurva advise founders on LP concentration limits? When is one LP too much of a fund? How does Apurva advise managers on selling a stake in the management company?

4.) As a fund of funds, how does Apurva approach fund portfolio construction today? How does this differ between the fund portfolio vs the direct portfolio? How does Apurva think about the compression of fundraising timelines both with GPs and Founders? Why does Apurva believe founders at the early-stage care less about firm brand today?

5.) How does Apurva feel about investing in managers he has not met in person? How does the GP/LP fundraising process need to change? How does COVID change the fundraising process for venture funds? How will LPs react to these changes?

Items Mentioned In Today's Show:

Apurva's Fave Book: Principles: Life and Work by Ray Dalio

Apurva's Most Recent Investment: Sourcegraph

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.

20VC: Why Few Firms Are Doing True Early Stage Investing Today, Why Founders Should Spend Time with Analysts When Raising & The Rise of Pre-Empting Rounds and How To Know When To Engage vs Wait with Anna Khan, General Partner @ CRV Aug 14, 2020

Show notes

Anna Khan is a General Partner @ CRV, one of the pre-eminent firms of Silicon Valley stretching over what is now an incredible 18 funds. In their portfolio, they have the likes of Airtable, Doordash, Postman and PillPack to name a few. As for Anna, prior to joining CRV, she spent an incredible 6 years at Bessemer investing in the likes of Intercom, NewVoiceMedia, RainforestQA and Zylo. If that was not enough, Anna is also the Founder & CEO @ Launch X Ventures, offering female entrepreneurs an immersive opportunity to learn how to raise capital for their businesses.

In Today's Episode You Will Learn:

1.) How Anna made her way into venture as an analyst with Bessemer and how that led to her scaling the venture ladder to now being GP @ CRV?

2.) How does Anna feel about the importance of analysts in venture? Should founders spend meaningful time with analysts? How should they determine which to spend time with? What were the biggest lessons Anna learned about venture and people from being an analyst at Bessemer?

3.) With the rise of rounds being pre-empted, how does Anna determine when to lean in and move on a deal vs when to wait? How does Anna determine when to stretch vs be disciplined on valuation? Why does Anna believe very few firms are "doing real early-stage investing" today?

4.) Why does Anna believe that there are so much fewer women in venture? How does Anna respond to the suggestion that it is a "pipeline problem"? How would Anna advise an all-white male partnership looking to truly change how they work? How does carry come into showing commitment?

5.) What advice does Anna give to people on developing your early network? Why does Anna believe VCs spending time with VCs is antithetical? How has Anna's investment decision-making process changed over the last 9 years? How does Bessemer's compare to CRV's?

Items Mentioned In Today's Show:

Anna's Fave Book: Why We Sleep: The New Science of Sleep and Dreams

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.

20VC: MongoDB CEO, Dev Ittycheria on Why Sometimes You Have To Be Inefficient To Be Effective, The 2 Different Types of Decisions and How Great Leaders Respond To Each & Why Value To Overhead Ratio Is The Metric To Use When Selecting Investors Aug 10, 2020

Show notes

Dev Ittycheria is the President and CEO @ MongoDB, recognized as the world's most popular next-generation database and the first database company to go public in over 26 years. Prior to their IPO, MongoDB raised from some of the best in the business including Sequoia, USV and NEA to name a few. As for Dev, before Mongo Dev was Managing Director at OpenView Venture Partners, Venture Partner at Greylock Partners, and CEO/Co-founder of BladeLogic, which was acquired by BMC for $900 million. Dev has also sat on some incredible boards including AppDynamics, athenahealth and BazaarVoice.

In Today's Episode You Will Learn:

1.) How Dev made his way into the world of startups? How Dev made his entry into the world of venture? How that led to his joining Mongo as CEO?

2.) How has Dev seen his style of leadership change over the last few years? What are the 3 core benefits of being vulnerable with your investors? Why does Dev believe you sometimes have to be inefficient to be effective? What element/trait would Dev like to improve and develop as a leader?

3.) Where does Dev believe the majority of leaders make mistakes when it comes to scaling their teams and orgs? How does Dev think about the debate of whether to promote internally or hire externally for a role? Why does Dev believe the asymmetry of information there is dangerous?

4.) What has been Dev's biggest lessons when it comes to the speed that information is relayed within orgs? How does this differ between good news and bad news? What can leaders do to create environments where bad news is shared freely? Where do many go wrong here?

5.) How does Dev advise founders on the criteria they should use to determine which investors to work with? What has been so impressive to Dev about working with Sequoia? How would Dev describe Roelof Botha's style of board membership? How can investors crucially build trust with their CEOs?

Items Mentioned In Today's Show:

Dev's Fave Book: High Output Management

As always you can follow Harry and The Twenty Minute VC on Twitter here!

20VC: Loom Founder Joe Thomas on Whether To Take Multi-Stage Money at Seed, How Early Stage Founders Should Select Their VC, How Sequoia Won The Loom Deal & The 3 Rules To Operate Remote Teams Successfully Aug 07, 2020

Show notes

Joe Thomas is the Founder & CEO @ Loom, the startup that helps you get your message across by making it easy to record instantly shareable videos. To date, Joe has raised over $68M from some of the valley's leading firms including Sequoia, Kleiner and Coatue as well as individuals such as Mathilde @ Front, Kevin & Mike @ Instagram and Dylan Field @ Figma to name a few. Prior to founding Loom, Joe was in LA as Director of Product at MyLife.com and before that Director of Operations at MediaPass. Due to Loom's success, Joe has been named to Forbes 30 Under 30 for Enterprise Tech.

In Today's Episode You Will Learn:

1.) How Joe made his way from the mid-West to the valley and came to found one of the hottest startups today in Loom?

2.) What does Joe believe are 3 rules to operate remote teams successfully? Why does Joe believe in remote + HQ as a model so much? How do the tools and culture need to change with this as a new format for work? How do leaders now need to learn to write more than ever before?

3.) How has fundraising fundamentally change in the world of COVID? What are the benefits? What can founders do and tools can they use to increase their chances of getting funded in a COVID world? What did Coatue do to build rapport and trust without meeting in person?

4.) What advice would Joe give to founders on how to pick their early VCs? How does Joe advise founders when it comes to accepting multi-stage money at seed? Why does Joe believe you need to be upfront with your VCs about their ability to build future ownership?

5.) Sequoia and Coatue led the Series B, how did the round go down many months before Joe and Loom planned to raise it? What did Sequoia do to win and close the deal? How did that as a founder make Joe feel? How does Joe advise VCs on what it takes to win the most competitive of deals?

Items Mentioned In Today's Show:

Joe's Fave Book: Enders Game, Think On These Things

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.

20VC: Steve Jurvetson on 20 Years of Friendship with Elon Musk, How To Analyse Market Timing, Why Venture Does Not Scale & Why He Has Never Sold A Share in Any Company He Holds Aug 03, 2020

Show notes

Steve Jurvetson is the Co-Founder @ Future Ventures who announced their debut and flagship $200M Fund in 2019. Steve's incredible portfolio includes the likes of SpaceX, Tesla, Planet, Memphis Meats, Hotmail, and the deep learning companies Mythic and Nervana. Steve also sits on the board of both SpaceX and Tesla. Prior to founding Future, Steve was the co-founder of renowned valley firm Draper Fisher Jurvetson where he led investments in 5 companies that went public in successful IPOs and several others that became billion-dollar acquisitions.

In Today's Episode You Will Learn:

1.) How Steve made his way into the world of startups and Silicon Valley and how that led to his creation of "The Lean Startup Movement"?

2.) How does Steve think about and assess market timing? How does Steve assess technical risk? Given the long term horizons of such deep tech projects, does Steve think we need to change the 10 + 2-year fund life structure? How would Steve like to see funds structured?

3.) Given the sheer size of outcomes if these plays work, how does Steve assess his own price sensitivity? How does Steve approach the challenge there is a lack of downstream investors for such deep tech projects? How does Steve try and catch an industry on the cusp of a transition?

4.) How does Steve assess his own relationship to money? How has it changed over the years? Why does Steve fundamentally believe that venture partnerships do not scale? Where do venture partnerships breakdown? How can one introduce cognitive diversity into a firm?

5.) Having worked with Elon Musk across both SpaceX and Tesla, what does Steve believe makes Elon one of the most gifted entrepreneurs of our time? What is Steve's most memorable moment from his many years of friendship with Elon? What have been his biggest takeaways from SpaceX and Tesla?

Items Mentioned In Today's Show:

Steve's Fave Book: Out Of Control: The New Biology of Machines, Social Systems, and the Economic World

Steve's Most Recent Investment: Prellis Biologic

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.

20VC: Why The Unbundling of Fintech Will Continue, How VCs Are Propping Up The Neo-Banking Industry & Why We Need A New Framework To Value Businesses Today with Clay Wilkes, Founder & CEO @ Galileo Jul 31, 2020

Show notes

Clay Wilkes is the Founder & CEO @ Galileo, the API standard for card issuing and digital banking, powering many of the leading global FinTech companies including Chime, TransferWise and Monzo to name a few. Prior to their reported $1.2Bn acquisition by SoFi, Clay raised just $86M in funding with Galileo from the likes of Accel and Ryan Smith @ Qualtrics, having run the company as a profitable company before that for over 15 years. Clay also has a keen interest in philanthropy having created the Galileo foundation with his wife in 2005.

In Today's Episode You Will Learn:

1.) How Clay made his way into the world of tech and startups more than 20 years ago and how he came to build the foundations for many fintechs today with Galileo?

2.) When looking at the current financial ecosystem does Clay believe we are in a phase of bundling or unbundling? Does Clay believe we will see the verticalisation of banking? Will every company become a payments company? Does Clay believe we will see consolidation in the space?

3.) What does Clay believe were the benefits of going 15 years withour raising VC money, building a profitable business? What are the trade offs? What could he have done if he had raised? With hindsight, does Clay wish he had raised earlier? Why was then the right time to raise?

4.) Why does Clay believe the discovery mechanism for VCs finding startups is broken? How did Clay select the venture firm he chose to work with, Accel? What advice does Clay give to board members when it comes to being the best board member to their founders?

5.) Why did Clay believe that selling to SoFi was the right decision? What are the benefits of the merger? How does Clay think about the competitive element that many of Galileo's current clients are competitors with SoFi? How do they remedy and solve for that today?

Items Mentioned In Today's Show:

Clay's Fave Book: Why Nations Fail: The Origins of Power, Prosperity and Poverty

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.

20VC: Brad Feld, Jerry Colonna and Tracy Lawrence on Depression and Mental Health, The Dangers of Tying Happiness To Milestones & Why Fear, Anxiety and Guilt Are Useless Emotions Jul 27, 2020

Show notes

Brad Feld is a Co-Founder and Managing Director @ Foundry Group, one of the most successful venture firms of the last decade with a portfolio including the likes of Zynga, Fitbit and Sendgrid to name a few. Brad is also a co-founder @ Techstars and prior to Foundry, he co-founded Mobius Venture Capital.

Tracy Lawrence spent the last 8 years as Founder & CEO @ Chewse, the startup that it effortless for office managers to order delicious food for their teams. Tracy grew the team to 300 people across 4 markets, raised millions in venture capital, and ultimately sold the business to Foodee.

Jerry Colonna is the CEO of Reboot.io where he is now the professional coach to some of the world's leading founders. Prior to his work with Reboot, Jerry was an early-stage VC co-founding Flatiron alongside Fred Wilson in 1996.

In Today's Episode You Will Learn:

1.) How did Brad, Jerry and Tracy all experience their first forms of depression? At what stage did it become a more prominent part of their life? Why do they think then was the catalyst?

2.) Why does Jerry believe that despite what people say, no one is crushing it? How can founders present their vulnerability as a strength? At what point did Tracy realise this? How did she convey her vulnerability to her team? Who is to blame for the lack of vulnerability and fear of opening up?

3.) How does Brad think about tying happiness to milestones? What are the biggest dangers of doing so? Does this mean one does not have goals? How does one balance between ambition and appreciating the present? How did Brad learn this when Amy asked for a divorce? How did he respond?

4.) Why does Brad believe fear, guilt and anxiety are useless emotions? What was the result of Tracy tying her mental state to her revenue line? How does Tracy think about the loneliness of being a founder? What does Brad believe is some of the biggest BS in the industry?

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.

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