1,188 episodes

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.

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

    • Business
    • 4.4 • 439 Ratings

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.

    20VC: How I Lost Airbnb at Seed Because of an Exploding Term Sheet | Investing Lessons from Roelof Botha & Peter Thiel | Why VC is Less Collaborative Than Ever and Great Companies Are Being Destroyed by Too Much Cash with Kevin Hartz @ A*

    20VC: How I Lost Airbnb at Seed Because of an Exploding Term Sheet | Investing Lessons from Roelof Botha & Peter Thiel | Why VC is Less Collaborative Than Ever and Great Companies Are Being Destroyed by Too Much Cash with Kevin Hartz @ A*

    Kevin Hartz is a Co-Founder and General Partner at A*, an early-stage venture capital firm. Prior to founding A*, Kevin co-founded Eventbrite, a publicly traded company, and served as the CEO for the first 11 years of the company. Before Eventbrite, Kevin co-founded Xoom, a money remittance company that was acquired by PayPal in 2015 for over $1BN. Kevin is also a prolific angel investor having backed companies such as PayPal, Airbnb, Pinterest, Ramp, Trulia, and Anduril at the seed stage, and was an early investor in Uber, Palantir, SpaceX, Square, Gusto and many others.

    In Today's Episode with Kevin Hartz We Discuss:
    1. What Makes the Best Founders:

    What questions does Kevin always ask founders in the investment process? Does Kevin prefer serial or first time founders? Why? Does Kevin prefer founders who are new to a problem or who are insiders and experts? When Kevin has gotten a founder bet wrong, what did he not see that he should have seen?
    2. The Exploding Term Sheet That Cost $10BN:

    How did an exploding term sheet for the seed round of Airbnb cost Kevin $10BN? What did Kevin see in the seed round of Airbnb that so few other investors saw? Does Kevin agree that the best businesses often start off as ridiculous or toys?
    3. From World's Greatest Angel to VC with $600M AUM:

    Why does Kevin think a barbell strategy of Seed and Series C is best today? Does Kevin agree that the Series B and growth stage is dead today? Why does Kevin strongly disagree that seed is the hardest stage of the market? Why does Kevin think that venture is less collaborative than ever? How does Kevin approach when to sell vs when to hold a position? What are his biggest lessons from seeding and holding Opensea?
    4. Learning From the World's Best Investors:

    What have been Kevin's lessons from his relationship with Peter Thiel? What have been Kevin's biggest takeaways from investing alongside Roelof Botha in many deals? What have been Kevin's biggest lessons from watching and observing the great Pierre Lamond?  

    • 1 hr 2 min
    20Product: How Canva Builds Products: Lessons Learned, What Works? What Flopped? The Top 5 Product Lessons in Scaling to 185M Monthly Active Users with Canva Co-Founder and Chief Product Officer, Cameron Adams

    20Product: How Canva Builds Products: Lessons Learned, What Works? What Flopped? The Top 5 Product Lessons in Scaling to 185M Monthly Active Users with Canva Co-Founder and Chief Product Officer, Cameron Adams

    Cameron Adams is Chief Product Officer and co-founder of Canva where he is responsible for heading up the design and product teams. Since launching in 2013, Canva’s global community has grown to over 185 million monthly users in over 190 countries. In 2021, Canva was valued at $40 billion, following a $200m funding round. This saw it become one of the most valuable private software companies in the world. Prior to joining Canva, Cameron found himself working closely with Lars and Jens Rasmussen (co-founders of Google Maps) to realise the design vision for Google Wave.

    In Today's Episode with Cameron Adams:
    1. From Accidental Joining to Most Valuable Private Company:

    How did Cameron go from working on Google wave with Lars Rasmussen to co-founding Canva with Mel and Cliff? What was the single closest near-death experience in the life of Canva? Why did Canva fail as a social network? What did Cameron learn from that?
    2. How to Create Users that Truly Love Your Products:

    What have been Canva's biggest lessons on what it takes to do world class onboarding? What is Cameron biggest advice to founders on how to create moments of delight in your product? Is simplicity always best in product? What, when made more complex, is better for the user?
    3. Scaling Canva into the Enterprise:

    What are the biggest product changes that are required to move into enterprise? What does Cam know about moving up market that he wishes he had known when he started? What are the biggest product and design mistakes founders make when making the transition from PLG to enterprise sales?
    4. AI Changes Everything: More Money or Better Products Only

    Who will win the foundation model layer landscape? What will it be in 10 years? Will companies actually make more revenue from having AI in products or will it just create better products? How does Canva's implementation of AI in their products impact the margins of their products?  

    • 49 min
    20VC: Brex CEO Pedro Franceschi on What Brex Needs to do to be a Public Company | Brex vs Ramp: Who Wins and How Does it Play Out | Battling Founder Mental Health and The Importance of Secondaries for Founders

    20VC: Brex CEO Pedro Franceschi on What Brex Needs to do to be a Public Company | Brex vs Ramp: Who Wins and How Does it Play Out | Battling Founder Mental Health and The Importance of Secondaries for Founders

    Pedro Franceschi is the Co-Founder and CEO @ Brex, the AI-powered spend platform with tens of thousands of customers, including DoorDash, Coinbase, Robinhood and Roblox. Pedro has raised over $1.2BN for the company from the likes of Greenoaks, Ribbit, DST, Bond and YC. The latest reported valuation was $12.3BN. Before Brex, Pedro was the first person to “jailbreak” the iPhone 3G in Brazil and co-founded payments company Pagar.me with Dubugras when he was 15. In three years, Pedro scaled it to over 100 people and US$1.5 billion in transactions processed.

    In Today's Episode with Pedro Franceschi We Discuss:
    1. The Challenge is in Your Own Head:

    Why does Pedro believe all founders underestimate their own mental health? When was Pedro most anxious/depressed in the Brex journey? Why? What have been the single biggest needle movers for increasing his own mental health? How does Pedro advise other founders struggling with their own mental health?
    2. From a 13-Year-Old Hacker in Brazil to Billionaire in LA:

    How did Pedro come to make $200K on the internet when he was just 12? Does Pedro agree that the best founders always started entrepreneurial pursuits young? How does Pedro reflect on his own relationship to money today? How has it changed? Pedro has famously taken large secondaries, how did that impact his mindset? How does Pedro advise other founders and VCs when it comes to secondaries?
    3. The Importance of the Idea: What Everyone Misunderstands:

    What does Pedro mean when he says everyone does not appreciate enough how important the idea selection process is? How does he advise founders entering this process? Why does Pedro believe it is not that easy for founder to just pivot to a new idea? How did YC almost miss out on investing in Brex, now a $12BN company, due to the original idea?
    4. Brex vs Ramp: Who Wins:

    How does Pedro feel when I say, "Ramp have gotten ahead on marketing and visibility"? Why does Pedro believe that "Ramp is a marketing company"? What does he mean when he says "great products will win over time"? Why does Pedro fundamentally disagree with Ramp's positioning of the best companies focus on saving and their giving away their software for free? How does this market play out over time? Winner take all or gains split across several?  

    • 50 min
    20VC: Why We Are in a Bubble & Now is Frothier Than 2021 | Why $1M ARR is a BS Milestone for Series A | Why Seed Pricing is Rational & Large Seed Rounds Have Less Risk | Why Many AI Apps Have BS Revenue & Are Not Sustainable with Saam Motamedi @ Greyloc

    20VC: Why We Are in a Bubble & Now is Frothier Than 2021 | Why $1M ARR is a BS Milestone for Series A | Why Seed Pricing is Rational & Large Seed Rounds Have Less Risk | Why Many AI Apps Have BS Revenue & Are Not Sustainable with Saam Motamedi @ Greyloc

    Saam Motamedi is a General Partner at Greylock, where he has led investments in Abnormal Security (incubated at Greylock), Apiiro Security and Opal Security, as well as AI companies like Adept, Braintrst, Cresta, Predibase, Snorkel, and more. Before Greylock, Saam founded Guru Labs, a machine learning-driven fintech startup, and worked in product management at RelateIQ, one of the first applied AI software companies.

    In Today's Conversation We Discuss:
    1. Seed Today is Frothier than 2021:

    How does Saam evaluate the seed market today? With seed pricing being so high, how does he reflect on his own price sensitivity? When does he say too much and does not do it? Despite seed pricing being higher than ever before, why does Saam believe it is rational? How has the competition at seed changed in the last few years?
    2. Series B and Growth are not a Viable Asset Class Today:

    Why does Saam believe that you cannot make money at Series B today? Why has pricing gone through the roof? Who is the new competition? When does it make sense to "play the game on the field" vs say this is BS and do something else? What would need to happen in the public markets for Series B to be a viable asset class again?
    3. Markets vs Founders: The Billion Dollar Mistake and Lessons:

    How does Saam prioritise between founder vs market? What have been Saam's biggest lessons when it comes to market sizing and timing? What is Saam's biggest miss? How did it change his approach and company evaluation? Which other VC would Saam most like to swap portfolios with? Why them?
    4. Saam Motamedi: AMA:

    What does Saam know now that he wishes he had known when he got into VC? Saam has had a meteoric rise in Greylock, what advice does Saam have for those younger investors look to really scale within a firm? Sourcing, selecting and servicing: Where is he best? Where is he worst? Why does Saam believe that most VCs do not add value? 20VC: Why We Are in a Bubble & Now is Frothier Than 2021 | Why $1M ARR is a BS Milestone for Series A | Why Seed Pricing is Rational & Large Seed Rounds Have Less Risk | Why Many AI Apps Have BS Revenue & Are Not Sustainable with Saam Motamedi @ Greylock

    • 1 hr 6 min
    20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge

    20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge

    Mark Roberge is a Co-Founder and Managing Director at Stage 2 Capital and a Senior Lecturer at the Harvard Business School. Prior to these roles, Mark was the founding CRO at HubSpot, where he scaled ARR from $0 to $100 million and expanded his team from 1 to 450 employees. Mark was ranked #19 in Forbes' Top 30 Social Sellers in the World. He was also awarded the 2010 Salesperson of the Year at the MIT Sales Conference.

    In Today's Episode with Mark Roberge We Discuss:
    1. Biggest Lessons Scaling Hubspot to $100M in ARR:

    What are Mark's biggest lessons in what worked in their sales strategy in scaling to $100M in ARR? What elements of Hubspot's sales strategy did not work? What would he have done differently with the benefit of hindsight? What does Mark know now that he wishes he had known when he started at Hubspot?
    2. How the Best Startups Scale into Enterprise:

    What are the single biggest mistakes startups make when scaling into enterprise? When is the right time? What do founders get most wrong on timing of scale into enterprise? What do you need to have in place both from a team and product perspective to make the transition?
    3. Second Product and Second Channel:

    When is the right time to launch the second product? Why does Mark believe that you should be turning down customers in the early days? Why is not every customer right for your company? How does Mark think about channel diversification? Does Mark agree you only need one channel to scale to $50M in ARR and two to scale to $100M in ARR?
    4. 99% of SaaS Founders Do Partnerships Wrong:

    What are the single biggest mistakes founders make when doing channel partnerships? What can and should they do to set channel partnerships up for success? What do the channel partners need to have to be equipped to sell the partner solution? What level of buy-in and from who on the channel partner side is needed for the partnership to be successful? What did Mark learn from Hubspot's partnership with Salesforce scaling to 10% of Hubspot's revenue?  

    • 40 min
    20VC: ServiceTitan Would Not Be the Success if We Raised VC Earlier: How to Build a Dominant Vertical SaaS Business, How to Master Going Into Enterprise, When & How to Launch Second Products with Ara Mahdessian, Co-Founder @ServiceTitan

    20VC: ServiceTitan Would Not Be the Success if We Raised VC Earlier: How to Build a Dominant Vertical SaaS Business, How to Master Going Into Enterprise, When & How to Launch Second Products with Ara Mahdessian, Co-Founder @ServiceTitan

    Ara Mahdessian is the Co-Founder and CEO @ ServiceTitan, one of the great vertical SaaS business of the last decade. Today the company powers over 11,800 trade customers and has raised over $1.4BN from some of the best including Bessemer, Battery, Index, ICONIQ and more. Their latest valuation pegged the business at a reported $7.3BN.

    In Today's Episode with Ara Mahdessian We Discuss:
    1. We Did Not Want To Raise VC Money:

    Why did Ara not want to raise VC funding in the early days? What convinced Ara to change his mind? Why did he choose Byron and Bessemer? Does Ara believe that ServiceTitan would have been the success that it is, if it had raised in today's market, a $5M on $25M seed round? What would they have done differently?
    2. How to Master Going Upmarket:

    What are Ara's biggest lessons on what it takes to go upmarket? How does the product need to change? How does the org of the company change? When is the right time to go upmarket? What did ServiceTitan get wrong in their move into enterprise? What did Ara learn from this?
    3. How to Build a Brand in SaaS and Have Premium Pricing:

    What are some of Ara's biggest lessons in how to build the best brand in vertical SaaS? What works in brand building in SaaS? What does not? What would he do differently? What have been Ara's biggest lessons on pricing? ServiceTitan is 3x their competitors, how does Ara think about what is required to have such premium pricing?
    4. How to Master the Second Product & Be the Best at Customer Success:

    When is the right time to do a second product? Why is it too late to wait for PMF with your first product to do the second product? What product did ServiceTitan wait too long to release? What did they learn? What product did they release too early? What did they learn? What are the two core reasons why customer success is the most important element in a business?
    5. The Core Pillars of Great Leadership:

    Why do product builder founders have such an increased chance of success in startups? Why do you have to have expertise in the domain you are hiring for to hire the best? What does truly great leadership mean to Ara today? How has his style of leadership changed? What has Ara learned from soccer that he has applied to being a CEO?  

    • 51 min

Customer Reviews

4.4 out of 5
439 Ratings

439 Ratings

AH_12 ,

Asparagus from Veggie Tales

I’m almost certain the host is the voice actor for the asparagus from veggie tales

Arj-Un ,

Must listen for any founders.

Harry is simply brilliant at this. I’ve learnt more as a founder listening to this podcast than reading a plethora of books. His curation of questions, guest list, and applicability of content to real world problems that founders face on their journey is unmatched. It is timeless in that it keeps with the latest trends in the industry. When you’re on a walk, a drive, or simply with a few minutes on hand, this podcast will help you realize new pathways applicable to your journey. Whether you’re a first time founder or a serial entrepreneur, add this to your collection of knowledge bases. You will be thankful!

Adi rates ,

Too good to miss!

Just heard my first show, the Ultimate Hiring Playbook with Matteo Franceschetti and I was glued to both the content and the delivery. Harry Stebbings packed dozens of high value questions and Matteo delivered as much good insights as he possibly could.

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