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20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless

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

Release Date: 05/15/2024

20Product: Loom CPO Janie Lee on Three Core Skills that Make the Best PMs, How to Find, Pick and Train the Best PM Talent and Lessons from OpenDoor and Rippling on Product Breadth, Pricing and Talent Density show art 20Product: Loom CPO Janie Lee on Three Core Skills that Make the Best PMs, How to Find, Pick and Train the Best PM Talent and Lessons from OpenDoor and Rippling on Product Breadth, Pricing and Talent Density

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

Janie Lee is the Head of Product and the owner of the Self-Serve business at Loom. Janie previously worked at Rippling, leading the Identity Management and Hardware teams. Prior to that, she worked at Opendoor launching markets and developing pricing algorithms. During this time, Opendoor scaled from 2 to 20+ markets, $5B+ revenue, and 1500+ employees. In Today's Episode with Janie Lee We Discuss: 1. Inside the Product Building Machine of Rippling and Opendoor: What are Janie's single biggest product lessons from Rippling? How do they build so much product so fast? Can you have...

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20VC: Scale's Alex Wang on Why Data Not Compute is the Bottleneck to Foundation Model Performance, Why AI is the Greatest Military Asset Ever, Is China Really Two Years Behind the US in AI and Why the CCPs Industrial Approach is Better than Anyone Else's show art 20VC: Scale's Alex Wang on Why Data Not Compute is the Bottleneck to Foundation Model Performance, Why AI is the Greatest Military Asset Ever, Is China Really Two Years Behind the US in AI and Why the CCPs Industrial Approach is Better than Anyone Else's

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

Alex Wang is the Founder and CEO @ Scale.ai, the company that allows you to make the best models with the best data. To date, Alex has raised $1.6BN for the company with a last reported valuation of $14BN earlier this year. Scale tripled their ARR in 2023 and is expected to hit $1.4BN in ARR by the end of 2024. Their investors include Accel, Index, Thrive, Founders Fund, Meta and Nvidia to name a few. In Today's Show with Alex Wang We Discuss: 1. Foundation Models: Diminishing Returns: What are the three core pillars that can meaningfully improve foundation models performance? Why is...

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20VC: Reid Hoffman on Foundation Models: Who Wins & How Do Incumbents Respond | The Inflection AI Deal: How it Went Down | Why Trump is a Threat to Democracy | The Future of TikTok | Lessons from Sam Altman, Brian Chesky and the OpenAI Board show art 20VC: Reid Hoffman on Foundation Models: Who Wins & How Do Incumbents Respond | The Inflection AI Deal: How it Went Down | Why Trump is a Threat to Democracy | The Future of TikTok | Lessons from Sam Altman, Brian Chesky and the OpenAI Board

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

Reid Hoffman has been one of the most impactful people in technology over the last two decades. He is the Co-Founder of Linkedin (acq by Microsoft for $26BN) and Co-Founder of Inflection.ai. As an investor, Reid has backed the likes of Facebook, Airbnb, Zynga and more. Reid is also a Board Member @ Microsoft and was on the board of OpenAI. In Today's Show with Reid Hoffman We Discuss: 1. Foundation Models: Commoditisation, Business Models, Incumbents: Does Reid believe we are seeing the commoditization of foundation models? Is it too late for new foundation models to be born today?...

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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 show art 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

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

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: From NASCAR to Silicon Valley SDR 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...

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20VC: Perplexity's Aravind Srinivas on Will Foundation Models Commoditise, Diminishing Returns in Model Performance, OpenAI vs Anthropic: Who Wins & Why the Next Breakthrough in Model Performance will be in Reasoning show art 20VC: Perplexity's Aravind Srinivas on Will Foundation Models Commoditise, Diminishing Returns in Model Performance, OpenAI vs Anthropic: Who Wins & Why the Next Breakthrough in Model Performance will be in Reasoning

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

Aravind Srinivas is the Co-Founder & CEO of Perplexity, the conversational "answer engine" that provides precise, user-focused answers to queries. Aravind co-founded the company in 2022 after working as a research scientist at OpenAI, Google, and DeepMind. To date, Perplexity has raised over $100 million from investors including Jeff Bezos, Nat Friedman, Elad Gil, and Susan Wojciki. In Today’s Episode with Aravind Srinivas We Discuss: Biggest Lessons from DeepMind & OpenAI What was the best career advice Sam Altman @ OpenAI gave Aravind? What were Aravind’s biggest...

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This Week in SaaS: PluralSight Goes to Zero, Salesforce and Mongo Hit Hard, The Next IPO Candidates and How Do We Solve the Problem of Liquidity in Venture Capital show art This Week in SaaS: PluralSight Goes to Zero, Salesforce and Mongo Hit Hard, The Next IPO Candidates and How Do We Solve the Problem of Liquidity in Venture Capital

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

 is one of the OG SaaS investors with all of his first five investments turning into unicorns with Pipedrive, Algolia, Talkdesk, Salesloft and RevenueCat all in his portfolio.  is the largest global community in SaaS and he has taught a generation the fundamentals of SaaS on saastr.com. In Our First Ever Episode of This Week in SaaS 1. PluralSight Goes to Zero: WTF happened to PluralSight? How did it go from $3.5BN to $0? Will this have a wider impact on the willingness of PE to buy tech companies? Who are the next contenders to go from hero to zero? Zendesk? Anaplan?...

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20Growth: The Six Channels Startups Need to Dominate to Grow, Why the Best Growth Talent Never Comes from Marketing or Product, Who and How to Hire Growth Leaders and Teams and Why in a World of AI, Growth is More Science than Art with Matt Lerner show art 20Growth: The Six Channels Startups Need to Dominate to Grow, Why the Best Growth Talent Never Comes from Marketing or Product, Who and How to Hire Growth Leaders and Teams and Why in a World of AI, Growth is More Science than Art with Matt Lerner

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

Matt Lerner is one of the OGs of growth having spent 11 years leading growth teams at PayPal. Post PayPal, Matt led the growth marketing program at 500 Startups. He is also the bestselling author of Growth Levers and How to Find Them. Today, Matt is the Co-Founder and CEO of SYSTM, an accelerator program helping startups find their growth drivers.  In Today’s Episode with Matt Lerner We Discuss: From Philosophy Student to PayPal Growth Leader: How did Matt make his way into the world of growth? What were Matt’s biggest lessons from 11 years at PayPal? What did Matt know now...

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20VC: Former Meta CTO, Schrep on Why Climate is a $10TRN Problem, Operating Lessons Scaling Products to Billions at Meta and Why the Best Leaders are Like Music Conductors show art 20VC: Former Meta CTO, Schrep on Why Climate is a $10TRN Problem, Operating Lessons Scaling Products to Billions at Meta and Why the Best Leaders are Like Music Conductors

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

Mike Schroepfer (Schrep) is the Founder & Partner @ Gigascale Capital, a new kind of climate-focused investment firm. Prior to Gigascale, Mike was the CTO @ Meta where he scaled products to billions of users, shipped millions of units of consumer hardware, constructed tens of millions of sq ft of data centres, built teams of up to 35,000, and made breakthroughs in AI. Before Meta, Mike led engineering at Mozilla and founded a company acquired by Sun Microsystems. In Today's Show with Mike Schroepfer We Discuss: 1. Lessons from Mark Zuckerberg and Meta: What are Schrep's biggest...

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20VC: Why Seed is Systemically Broken | Why Pricing is Worse Than Ever and There is More Funding Than Ever | Benchmarks for Churn, Retention and Growth Rates - Good vs Great | Why Last Vintage for Private Equity Will Suck with Jason Lemkin show art 20VC: Why Seed is Systemically Broken | Why Pricing is Worse Than Ever and There is More Funding Than Ever | Benchmarks for Churn, Retention and Growth Rates - Good vs Great | Why Last Vintage for Private Equity Will Suck with Jason Lemkin

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

Jason Lemkin is one of the OG SaaS investors with all of his first five investments turning into unicorns with Pipedrive, Algolia, Talkdesk, Salesloft and RevenueCat all in his portfolio. SaaStr is the largest global community in SaaS and he has taught a generation the fundamentals of SaaS on saastr.com. In Today's Episode with Jason Lemkin We Discuss: 1. Growth Rates and Churn Rates: Average/Good/Great: What is a growth rate that would excite Jason in a SaaS company? What is average? What levels of churn would worry Jason to see? What would excite him to see? What does Jason never...

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20VC: OpenAI's Sam Altman, Mistral's Arthur Mensch and more discuss: Will Foundation Models Be Commoditised | Which Startups Are Threatened vs Enabled by OpenAI | Is the Value in the Infrastructure or Application Layer? show art 20VC: OpenAI's Sam Altman, Mistral's Arthur Mensch and more discuss: Will Foundation Models Be Commoditised | Which Startups Are Threatened vs Enabled by OpenAI | Is the Value in the Infrastructure or Application Layer?

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

 is the CEO @ OpenAI, the company on a mission is to ensure that artificial general intelligence benefits all of humanity. OpenAI is one of the fastest-scaling companies in history with a valuation of $90BN and $2BN+ in revenue.  is the COO @ OpenAI and the man responsible for the incredible scaling of sales, GTM, partnerships and business to today being over $2BN in revenue. Arthur Mensch is the Co-Founder and CEO of . Since its inception in May 2023, Mistral has raised over $520M in funding from investors like Andreeseen Horowitz, General Catalyst,, and Microsoft with a...

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More Episodes

Dan Siroker is the Co-Founder and CEO @ Limitless, a personalized AI powered by what you’ve seen, said, or heard. For his latest funding round, Dan took an unusual approach resulting in 1,000 preliminary offers with valuations as high as $1BN — and resulted in a $350 million Series A valuation. Prior to founding Limitless, Dan was the Founder of Optimizely, scaling the company to $120M in ARR and raising from some of the best in the business including Peter Fenton @ Benchmark who led the Series A.

In Today's Episode with Dan Siroker We Discuss:

1. Serial Entrepreneurs are More Investable:

  • Why would Dan always prefer to invest in serial entrepreneurs than first time founders?
  • How do serial entrepreneurs approach team building and size of team differently?
  • How do serial entrepreneurs approach focus and prioritisation differently?
  • How do serial entrepreneurs approach pivoting differently to first time founders?
  • What is Dan's advice from Elad Gil and YC's Dalton Caldwell on when to pivot?

2. The Secret to Fundraising: How to Speak VC

  • Should founders always be raising?
  • What is the right thing to respond to investors when they reach out to you outside of a round?
  • What question are investors really asking when they ask, how much are you raising?
  • How should founders approach valuation, what should they say when they are asked for it?
  • How can founders create urgency in a funding round? What works? What does not?

3. How to Raise the Best Funding Round:

  • Should founders engage with associates or only worth it with decision-makers?
  • Why should founders always choose the investor who is on the early arc of their career?
  • Why was Dan's first meeting with Peter Fenton the best meeting he has ever had with a VC?
  • Why does Dan believe that taking the highest price is never the right answer?
  • To what extent does having a true Tier 1 VC lead your round, change the game for your company?

4. Dan Siroker: AMA:

  • How did becoming a father change the way that Dan operates?
  • Why is Dan scared we might see technological progress stall for the next 20 years?
  • Why did Dan not do YC the second time around with Limitless?
  • What is the story of how Optimizely nearly bought Amplitude?