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Harry Stebbings

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

Simon Sinek is an optimist and author, as we discuss in the show today. Simon is best known for his TED Talk on the concept of WHY (62M views), and his video on millennials in the workplace (80M views in 7 days). Simon is also a bestselling author including global bestseller Start with WHY, Leaders Eat Last and The Infinite Game. In addition, Simon is the founder of The Optimism Company, a leadership learning and development company, and he publishes other inspiring thinkers and doers through his publishing partnership with Penguin Random House called Optimism Press.
 
 
 In Today's Discussion with Simon Sinek We Discuss: 
 
 
1. The Makings of Simon Sinek:
 
 
 
 • In what ways does Simon believe that his parents and upbringing shaped who he is today?
 • What does Simon want to be when he grows up?
 • What was the catalytic moment to the "Simon Sinek brand"? When was that big break moment?
 
 
 
2. Identity:
 
 
 
 • Simon has said before, "I define myself by who I am and not what I do". Is it wrong to define yourself by what you do?
 What do you do if you do not know who you are? • What do you do if you do not like the answers to who you are?
 • Is it possible to change who you are? What does that process look like?
 • What is Simon's biggest advice to those looking to find a greater sense of self and identity?
 
 
 
3. Trust:
 
 
 
 • Does Simon start relationships with inherent trust and it is there to be lost or no trust and it is there to be gained over time?
 • When has someone broken Simon's trust? How did it impact how he approaches trust today?
 • In the case of cheating in a relationship, does Simon believe it is possible to regain trust over time?
 • Simon has said before, "trust is built on telling the truth". Does it ever make sense or is even right to tell a little white lie in a relationship?
 
 
 
4. Creating Safe Spaces:
 
 
 
 • How can we create safe spaces for our partners to be their full selves?
 • Does this differ professionally and personally?
 • What are the biggest mistakes people make in building safe spaces?
 
 
 
5. Listening:
 
 
 
 • What does great listening in a relationship mean? How can we do it better?
 • Often people jump from listening to solution mode, is that wrong?
 • Why does Simon have a rule of “no crying alone”. What does it do and how is it productive? When was the last time Simon cried?
 
 
 
6. Simon Sinek: AMA:
 
 
 
 • What is success to you?
 • Can one be “successful” and unhappy?
 • What is the difference between happiness and joy?

20VC: Simon Sinek on Trust; How it is Gained and Lost | Why Millennials Avoid Conflict | How to Listen Effectively | What Makes The Best Feedback and How to Provide It | Why Humans Do Not Change & How To Find Out Who You Really Are

Marc Benioff is one of the iconic founders and visionaries of our time. From the founding of Salesforce 25 years ago, Marc has in many ways created an entire industry. He has scaled the company to a market cap of $346BN, $38BN in revenue and over 72,000 employees. 
 
Ask Me Anything with Marc Benioff: 
 
The Future of Models:
 
 1. 

Why does Marc believe we are at the upper end of LLMs and they are commoditising?
 2. 
 3. 

Why does Marc believe the future of models is many smaller, verticalised models specialised in different areas?
 4. 
 5. 

OpenAI vs Anthropic vs Xai. Which would Marc buy and which would he short?
 6. 
 7. 

What is the single biggest barrier to Salesforce winning the AI war in the next 10 years?
 8. 
 
The Future of Agents:
 
 1. 

What does Salesforce need to do to prevent becoming a database in the next generation of AI? 
 2. 
 3. 

To what extent do agents hurt vs help Salesforce?
 4. 
 5. 

What do very few people understand about agents that is very important?
 6. 
 
The Future of Labour: 
 
 1. 

Will Salesforce replace it’s human labour with digital labour? Will Salesforce be bigger or smaller in 10 years time, people wise?
 2. 
 3. 

Why does Marc believe that layoffs are a crucial tool for CEOs to win?
 4. 
 5. 

How will a future of digital labour change the pricing model of SaaS tools today?
 6. 
 
Management Lessons from Marc Benioff:
 
 1. 

How did one meeting with Steve Jobs change how Marc views leadership?
 2. 
 3. 

How does Marc analyse the required mindset to win as a CEO today?
 4. 
 5. 

What has Marc changed his mind on most in the last 12 months?
 6.

20VC: Salesforce Founder Marc Benioff on The Future of LLMs | The Future of Agents | The Future of Labour | Management Lessons from Steve Jobs

Torsten Reil is the Co-Founder and Co-CEO of Helsing, a new type of defence company providing artificial intelligence to protect our democracies. Torsten has raised over $825M from the likes of Prima Materia, Elad Gil, Accel and General Catalyst. Previously Torsten founded NaturalMotion, one of the UK's most successful games and technology start-ups. Torsten was named as one of MIT's Top 100 Innovators and is a member of the Munich Security Conference Innovation Board.
 
In Today’s Episode with Torsten Reil We Discuss:
 
1. The World Around Us: China, Russia and Trump:
 
 • 

What will happen between China and Taiwan?
 • 
 • 

What will happen between Russia and Ukraine?
 • 
 • 

How will a Trump administration impact the US’ commitment to fund European defence?
 • 
 • 

What conflict do people not pay enough attention to in the world today?
 • 
 
2. Are We Ready and What Needs to Be Done:
 
 • 

Are the west ready to fight against our adversaries as we stand today?
 • 
 • 

What do we need to do to equip ourselves? 
 • 
 • 

What needs to change in our defence budgets? Where do they need to go?
 • 
 • 

How does the procurement process for defence need to change?
 • 
 
3. The Future of War: 
 
 • 

Why does Torsten believe the future of war is contactless?
 • 
 • 

In the next wave of defence, what are the most important elements for allies to own? What elements concern Torsten the most?
 • 
 • 

What role does AI and autonomous play in the future of war?
 • 
 
4. Is Europe F********:
 
 • 

Why does Torsten believe that Europe’s biggest problem is ambition not capital?
 • 
 • 

Why does Torsten believ that we put too much weight on the location in which companies are founded? Why does it not matter?
 • 
 • 

How does Torsten respond to the statement that we do not have the depth of experienced talent in Europe to recruit?
 •

20VC: The Future of War: Are We Ready & What Needs to Be Done | China, Russia and Trump: What Happens Now | Raising $828M to Build the Defence Champion of Europe | Torsten Reil, Co-Founder @ Helsing

Guillaume Moubeche is the Founder of Lempire, a company he has bootstrapped in the most competitive market in technology and scaled to a staggering $30M in ARR. Guillaume has never raised primary funding for the business but sold $10M of secondary at a $150M valuation. Guillaume is also an angel investor and and best selling author. 
 
In Today’s Episode with Guillaume Moubeche:
 
1. How to Build a Sales Machine:
 
 • 

What is the biggest mistake founders make when crafting their ideal customer profile?
 • 
 • 

What are Guillaume’s biggest lessons in scaling from $0-$1M in ARR? 
 • 
 • 

Why are most founders afraid to sell? What can they do to overcome this?
 • 
 • 

What is the ultimate equation to success in sales?
 • 
 
2. How to Build a Content Machine:
 
 • 

How does Guillaume come up with ideas for new content?
 • 
 • 

How does he structure his content creation time? 
 • 
 • 

How does Guillaume advise founders on which platform and content type they should focus on? What are the biggest mistakes they make?
 • 
 • 

How does Guillaume think about content repackaging and reposting? What have been some of the biggest lessons in how to get the max out of existing content?
 • 
 
3. How to Build a Hiring Machine:
 
 • 

Why does Guillaume think you should pay people well above market rate? What does it allow you to do as their employer?
 • 
 • 

Why does Guillaume think in 90% of times, more people equals more problems?
 • 
 • 

What have been Guillaume’s biggest hiring mistakes? What did he learn?
 • 
 
4. Making $10M, Ironman and Family:
 
 • 

How does Guillaume reflect on his own relationship to money? How has it changed post making $10M? 
 • 
 • 

Why does Guillaume believe that endurance sports makes for better entrepreneurs?
 • 
 • 

When asked if all the sacrifices were worth it, how does Guillaume respond? What does his life not have yet that he would most like?
 •

20Growth: How to Scale to $30M ARR Bootstrapped through Content and Brand | The Ultimate Equation to Success in Sales and Why Most Founders Suck at Sales | Why You Should Overpay People and What That Means with Guillaume Moubeche @ Lempire

Reid Hoffman is one of the most impactful people in technology and startups. As a Founder he founded Paypal and Linkedin before moving to the investing side where he has led deals in Facebook, Airbnb and more. 
 
In Today’s Episode with Reid Hoffman We Discuss:
 
1. China and Tariffs:
 
 • 

Should the US ban Tiktok and other Chinese companies, given China banning US companies presence in their country?
 • 
 • 

How does Reid evaluate the rise of the Chinese car industry? What are his concerns?
 • 
 • 

How does Reid hope Trump uses tariffs to advantage the US position?
 • 
 • 

What is Reid concerned about what Trump could do with tariffs? What would be bad?
 • 
 
2. Elon Musk and DOGE:
 
 • 

What impact will Elon Musk have on the future of AI in America?
 • 
 • 

Why does Reid believe that it is impossible for DOGE to achieve it’s targets?
 • 
 • 

What should Elon must be given credit for? What does he not deserve credit for?
 • 
 • 

What are Elon’s greatest strengths? What are his greatest weaknesses?
 • 
 
3. The US Defence Budget and Ukraine:
 
 • 

Why does Reid believe that the US should reduce their defence budget?
 • 
 • 

Does Reid believe the US should continue to finance the war in Ukraine?
 • 
 • 

Should the US continue to subsidise NATO’s lack of defence spending?
 • 
 
4. NVIDIA and The Future of Chips:
 
 • 

Will NVIDIA be able to sustain their monopoly? 
 • 
 • 

What is the biggest threat to their position?
 • 
 • 

Should both the US and Europe have their own chip sovereignty?
 • 
 • 

How does Reid evaluate potential conflict between China and Taiwan impacting chip supply?
 • 
 
5. Nuclear, Quantum and Climate:
 
 • 

Why does Reid believe nuclear fusion can solve climate change?
 • 
 • 

Does Reid believe that with the rise of global conflict and AI, the importance of climate change is reduced in the attention of the world?
 • 
 • 

Why does Reid believe that AI does more to help than harm climate change? 
 • 
 • 

Why is Reid so excited for a future with quantum computing? 
 • 
 • 

What are the biggest dangers of quantum that we need to be mindful of?
 •

20VC: Reid Hoffman on The Trump Administration | Elon Musk and DOGE | The US Defence Budget, NATO and The War in Ukraine | China, Tariffs and TikTok | The Future of Chips, Nuclear Energy, Quantum Computing and Climate

Daniel Dines is the Founder & CEO @ UiPath, one of the most incredible journeys in startups. For 10 years, UiPath was a bootstrapped company that scaled to just $500K in revenue. Then it all changed, product market fit became obvious and the rest is history. The company went on to raise funding from Sequoia, Accel, Kleiner Perkins and more. Today, the company is worth over $10BN, listed on the NASDAQ and does $1BN+ in revenue.
 
In Today’s Episode with Daniel Dines We Discuss:
 
1. The Future of LLMs:
 
 • 

Why does Daniel believe that we are at the upper end of scaling laws and more compute will not lead to increased performance?
 • 
 • 

Does Daniel believe we will see a world of many specialised models or fewer generalist models?
 • 
 • 

OpenAI, Anthropic, Xai. Which would Daniel most want to invest in? Why them?
 • 
 
2. Is RPA F******* in a World of Agents:
 
 • 

What is the core difference between RPA and agents? How do the tasks they complete differ?
 • 
 • 

Why must we have a neutral meta layer coordinating RPA processes and agents?
 • 
 • 

Why will siloed applications like Salesforce be unable to expand beyond their initial function? 
 • 
 • 

Why does Daniel believe that agents will not complete tasks but make recommendations?
 • 
 
3. The Future of Work: WTF Happens with Agents:
 
 • 

How long will it be before agents are fully utilised in the enterprise?
 • 
 • 

What is the role of the human in a world of agents?
 • 
 • 

What are the single biggest concerns of enterprises considering implementing agents in their companies?
 • 
 • 

Why has GenAI not been successful in enterprise so far? Will this change?
 • 
 
4. Daniel Dines: The Billionaire Behind the Brand:
 
 • 

How does Daniel deal with the loneliness of being CEO?
 • 
 • 

What problem did Daniel struggle with for much of his twenties and thirties? How did he overcome it?
 • 
 • 

Why does Daniel fear that he is becoming more and more disconnected? 
 • 
 • 

Why does Daniel believe 1-1s are BS?
 • 
 • 

What is Daniel’s single biggest advice to a new parent today?
 •

20VC: UiPath's Daniel Dines on Why Agents Do Not Mean RPA is F***** | Why We Have Reached the Upper End of Scaling Laws | The Future of Work in an Agent World and What Everyone Misunderstands About Enterprise AI

Matt Plank is Rippling's Chief Revenue Officer where he oversees all Sales and Account Management functions in the US and Internationally. Matt joined Rippling in the very early days when Parker Conrad (founder) was building V1 in a basement with $0 in revenue. Today the company is a market leader with 100s of $Ms in ARR. Prior to Rippling, Matt was a Sales Director @ Zenefits where he helped the company scale to $70M in ARR. 
 
In Today’s Show with Matt Plank We Discuss: 
 
08:25 Challenges and Strategies in Outbound Sales
 
10:29 Building Effective Sales and Marketing Partnerships
 
13:37 Founders and Sales Playbooks: Who Should Create Them?
 
20:45 Pricing Strategies and Customer Success
 
24:43 Discounting and Urgency in Sales
 
33:57 Building Relationships for Successful Deals
 
34:22 Effective Deal Reviews: Asking the Right Questions
 
35:30 Pipeline Reviews: Frequency and Participants
 
35:59 Handling Deal Slippage: Acceptable vs. Non-Acceptable Reasons
 
39:17 Maintaining Morale in Volatile Times
 
42:14 Outbound Sales Strategy: Lessons Learned
 
46:03 Scaling Sales Teams: Hiring and Promoting
 
47:15 Challenges and Strategies in International Markets
 
01:00:45 Signs of Scaling Issues in Sales Leadership

20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank

Mike Maples is one of the OG seed investors of the last two decades. As a co-founding Partner at Floodgate, Mike has been on the Forbes Midas List eight times in the last decade. Some of Mike’s investments include Twitter, Twitch.tv, Clover Health, Okta, Outreach, Chegg, Demandforce, and Applied Intuition.
 
In Today’s Episode with Mike Maples We Discuss:
 
04:02 Does Seed Even Make Sense as an Asset Class? 
 
05:16 Fund Size and Strategy: How to Do a 10x Fund?
 
08:12 Follow-On Investments: Are they BS?
 
16:41 Finding Inefficiencies in the Market
 
26:31 Exit Strategies and Liquidity Events: When to Sell?
 
35:14 How Floodgate Lost Billions Missing Airbnb and Pinterest
 
35:43 3 Frameworks for Evaluating Startups
 
36:23 Case Studies: Zoom and Okta
 
43:34 How to Truly Analyse Product-Market Fit
 
45:22 Challenges with Overfunding Startups
 
50:02 2024 in Review: Company and Fund of the Year
 
54:25 Predictions for 2025

20VC: How To Do a 10x Seed Fund in 2025 | Three Frameworks to Evaluate Startups an Founders | Lessons from Losing Billions Missing Airbnb and Pinterest & Investing Lessons from Charlie Munger with Mike Maples @ Floodgate

Carvana is one of the most wild stories in the public markets. The company IPO’d with a market cap of $2BN before skyrocketing to $60BN, only for the company to lose 99% of it’s value hitting a bottom of $400M market cap. Today the company is stronger than ever and with a market cap of $41BN. Joining us in the hotseat is Dan Gill, Carvana’s CPO, the man who oversees all technology functions, as well as strategic partnerships for the business.
 
In Today’s Episode with Dan Gill We Discuss:
 
 1. 

From $60BN to $400M Market Cap:
 2. 
 • 

What did Carvana do that Dan wishes they had not done?
 • 
 • 

What did Carvana not do that Dan wishes they had done? 
 • 
 • 

How do you maintain morale in a team when the company has lost 99% of it’s value? 
 • 
 1. 

From $400M Back to $40BN Market Cap:
 2. 
 • 

What have been the core needle movers in Carvana’s market cap surging?
 • 
 • 

How does the Carvana business model benefit from economies of scale?
 • 
 • 

How does vertical integration of the different products Carvana sells change the margin structure of the business? 
 • 
 1. 

The Future of Carvana:
 2. 
 • 

Why does Dan believe there is a massive market for Cavana in selling new cars?
 • 
 • 

Why does Dan want to move into the peer to peer market, a market where so many before have failed?
 • 
 • 

Why does Dan think Carvana should sell Chinese cars on the platform if American citizens want to buy them? 
 • 
 • 

What revenue line does Carvana not have today that Dan believes will be the biggest in 10 years time? 
 • 
 1. 

Product Advice, North Star Metrics, Idea Selection:
 2. 
 • 

What is the product advice that Dan gives more than any other?
 • 
 • 

How does Dan advise startup founders on how to know they have the right north star metric? What is his framework?
 • 
 • 

How does Dan advise founders on how to select the right idea to work on?
 • 
 • 

What is Dan’s prioritisation framework for if an idea will have a larger enough impact and is therefore worthy of being worked on?
 •

20VC: Carvana: The Most Wild Story in Public Markets: From $60BN to $400M and Back to $40BN | The Biggest Opportunities, Mistakes and Challenges Ahead for One of the Public Market's Only 100x Investments

Mikey Shulman is the Co-Founder and CEO of Suno, the leading music AI company. Suno lets everyone make and share music. Mikey has raised over $125M for the company from the likes of Lightspeed, Founder Collective and Nat Friedman and Daniel Gross. Prior to founding Suno, Mikey was the first machine learning engineer and head of machine learning at Kensho technologies, which was acquired by S&P Global for over $500 million. 
 
In Today’s Episode with Mikey Shulman:
 
1. The Future of Models: 
 
 • 

Who wins the future of models? Anthropic, OpenAI or X?
 • 
 • 

Will we live in a world of many smaller models? When does it make sense for specialised vs generalised models?
 • 
 • 

Does Mikey believe we will continue to see the benefits of scaling laws?
 • 
 
2. The Future of UI and Consumer Apps: 
 
 • 

Why does Mikey believe that OpenAI did AI consumer companies a massive disservice?
 • 
 • 

Why does Mikey believe consumers will not choose their model or pay for a superior model in the future? 
 • 
 • 

Why does Mikey believe that good taste is more important than good skills?
 • 
 • 

Why does Mikey argue physicists and economists make the best ML engineers?
 • 
 
3. The Future of Music: 
 
 • 

What is going on with Suno’s lawsuit against some of the biggest labels in music?
 • 
 • 

How does Mikey see the future of music discovery?
 • 
 • 

How does Mikey see the battle between Spotify and YouTube playing out?
 • 
 • 

How does Mikey see the battle between TikTok and Spotify playing out?
 •

20VC: The Future of Foundation Models | The Future of AI Consumer Apps and Why OpenAI Did a Disservice to Them | The Future of Music: Spotify vs YouTube & Spotify vs TikTok: What Happens with Mikey Shulman @ Suno

Ashley Kelly is the VP of Global Sales Development at Rippling, the all-in-one platform for HR, IT, and finance. Before Rippling, Ashley played a crucial role in scaling Brex’s outbound sales from $2M to over $300M in ARR, and has hired over 800 SDRs during her time in some of the best tech companies in Silicon Valley, including Lever and Zenefits. 
 
In Today’s Episode with Ashley Kelly We Discuss:
 
 1. 

From NASCAR to Silicon Valley SDR
 2. 
 • 

How did Ashley make her way into the world of sales?
 • 
 • 

Why does Ashley think the best AEs and leaders start off as SDRs?
 • 
 • 

What is Ashley’s advice to new SDRs starting their jobs today?
 • 
 1. 

Age of AI: Is SDR Outbound Dead?
 2. 
 • 

Does Ashley agree that outbound is dead today? Is SDR dead?
 • 
 • 

How will AI change SDR? Why is Ashley hesitant to adopt AI?
 • 
 • 

Why does Ashley think founders should always build the first sales playbook?
 • 
 • 

What did Ashley mean by SDR is the 3rd pillar between sales and marketing? 
 • 
 • 

What does Ashley think most companies get wrong about outbound?
 • 
 1. 

SDR Hiring: Who, What, When & How
 2. 
 • 

When does Ashley think founders should hire their first SDR?
 • 
 • 

How does Ashley structure the hiring process? What questions does she ask?
 • 
 • 

What profile does Ashley look for when hiring for an SDR?
 • 
 • 

How does Ashley structure the finance package? How is it different for each team?
 • 
 • 

Why did Ashley avoid hiring SDRs with SDR experience? Why has she changed her mind?
 • 
 • 

What was Ashley’s biggest hiring mistake? What were her takeaways?
 • 
 1. 

Onboarding New SDR Hires
 2. 
 • 

How does Ashley onboard new SDR hires? What is her onboarding timeline?
 • 
 • 

How does Ashley set targets for new hires? When should they be fully productive? 
 • 
 • 

When does Ashley know if a new hire isn’t working?
 • 
 • 

What are common traits among Ashley’s most successful hires?
 •

The Twenty Minute VC

20Sales: How Rippling Built Their Sales Machine: How to Hire, Train and Manage the Best SDRs, What is the Right Comp Package for Sales Teams & The Playbook to Start and Scale Your SDR Team

20Sales: How Rippling Built Their Sales Machine: How to Hire, Train and Manage the Best SDRs, What is the Right Comp Package for Sales Teams & The Playbook to Start and Scale Your SDR Team

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