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

Nilan Peiris is Chief Product Officer at Wise, where he leads on growth across channels including product and platform. Prior to Wise, Nilan was VP Growth at HouseTrip, in charge of scaling the company’s growth in the European market. He’s also worked as Chief Marketing Technology Officer at Holiday Extras, where he was responsible for all areas of technology, marketing and customer acquisition. Nilan also advises a number of early-stage startups on growth and getting to traction.

1. Lessons Scaling Transferwise to the First 1M Users:

• What growth tactics worked in scaling Wise to 1M users?
• What growth tactics did not work? What did they learn?
• What did Wise not do that Nilan wishes they had done?
• What single product change completely changed the trajectory of their growth?

2. How to Use Content to Crush Competition:

• What are the two different types of content that all companies must now make?
• What are the single biggest mistakes companies make with content today?
• What do you do when your competition can spend 7-8x more on marketing?
• Is SEO and SEM dead today or does it still play the same prominent role?

3. Wise's Framework on How to Win at Performance Marketing:

• What have been Nilan's single biggest lessons on how to win in performance marketing?
• What are the biggest mistakes companies make today in performance marketing?
• When is the right time to diversify and add new channels?
• What level of channel concentration would concern Nilan to see?

4. The Secret to Adding More Products:

• When is the right time to add a second product?
• How does Nilan define great product marketing today?
• How can one do amazing and targeted product marketing with several products aimed at different customers?
• What are the single biggest mistakes that companies make with brand marketing?

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.

1. Wiz Rejects Google's $23BN Acquisition Offer:

• How does Jason analyse the price of the offer? $23BN for a $500M ARR business growing 120% YoY?
• What is the reasoning for Google in pursuing the acquisition?
• If Wiz had of proceeded in the process, what are the chances it would have made it through regulators?
• Why did Wiz walk away from the offer? If Jason were on the board, what would he have done?
• Is there a correlation between the downfall of Crowdstrike and Wiz turning down the offer?
• What does this mean for the M&A market moving forward?
• Will there be a secondary round now in place for Wiz at $23BN?

2. Crowdstrike: WTF Happens from Here:

• Did Crowdstrike manage the crisis in the right way? What would Jason have done differently?
• What is the bull case for Crowdstrike moving forward from this point?
• What are the bear case for the company? Could this snowball and be the end?
• What will this do to company requirements on having single point of failure solutions?
• Where will the market cap of Crowdstrike be at the end of 2024?

3. LegalTech: Show Me the Money: $1BN in a Single Day:

• Clio announced a $900M round at a $3BN valuation. How does Jason analyse this?
• What does Jason make of Harvey's $100M raise at a $1.5BN valuation?
• Why does Jason think 2025 will be the year for AI parity? Why will we see the majority of SaaS features be commoditised in 2025?
• What is the single biggest regret that Jason has in his investing career?

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.

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?

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.

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?

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.

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?

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.

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

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.

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?

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.

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?

Pat Grady is one of the most successful growth investors of the last decade. As the Head of Sequoia's growth investing practice, Pat has invested in companies with a combined market cap exceeding $250BN. Among Pat's immense portfolio is Hubspot, Snowflake, ServiceNow, Okta, Amplitude, Zoom and Qualtrics. Pat is also one of the best acquirers of talent in venture hiring Andrew Reed, Matt Huang, Julien Bek.

1. The Sequoia Investment Process:

• What is the Sequoia investment process today? How has it changed over time?
• What could be improved about the process? Where is it weak?
• What is the biggest strength of the process?
• How do Sequoia remove politics from the investment decision-making process?
• Are the best deals "contrarian"? What does Pat mean when he says you do not "get extra points for being contrarian and right"?

2. What Sequoia Look for When Investing:

• What is Pat's framework for assessing founders? How does it differ when investing early vs late?
• Team, traction, TAM, how does Pat rank the three when investing?
• What have been Pat's biggest lessons on market sizing? Does Pat take market timing risk?
• How much weight does Pat place on "traction" when investing? How sustainable is PMF?

3. The Three Core Pillars of Venture:

• Sourcing: What does Pat rank Sequoia for sourcing? Who is the best at sourcing in the firm?
• Selecting: How does Pat rank Sequoia at picking? How has it changed over time? What could Sequoia do to improve their picking ability?
• Servicing: What does Pat give Sequoia for their "value add"? To what extent does Pat truly believe that venture investors do add value?

4. Pat Grady: AMA:

• Pat has hired some of the best in the next generation of venture investors; what are his biggest lessons in what he looks for when hiring investing talent?
• What is his single biggest takeaway from working with Alfred Lin, Roelof Botha and Doug Leone?
• What are his biggest takeaways from working with Hubspot, Snowflake and ServiceNow?

Avi Eyal is Co-Founder and Managing Partner of Entrée Capital, an early-stage VC fund with a portfolio including the likes of Monday.com, Stripe, Coupang, PillPack, and Snap. From their $15M investment into Monday, Entrée distributed a whopping $1.5BN, one of their $45M funds is a whopping 37x DPI. Avi is one of the greatest venture investors you might not have heard about.

1. The Biggest BS "Rules" in Venture Capital:

• Why does Avi believe that it is BS for every deal to need to be a homerun and return the fund?
• Why does Avi believe that signalling is real and it is BS to suggest otherwise?
• Why does Avi believe that it is BS that ownership is crucial to make mega venture returns?
• Why does Avi believe that you do not have to win every deal to be one of the best in venture?
• Why should venture investors not manage the positions of their companies when they go public? Why is it BS to think they have asymmetric information when the company goes public?

2. What Makes the Best Founders:

• Does Avi prefer first or second time entrepreneurs? Why?
• Would Avi rather back a founder that is an expert in a market or one that is new to a market and has the naivety to not know what is hard?
• Are the best CEOs the best fundraisers?
• How does Avi rank the following when investing; team, market, traction and technology?
• When Avi has misread a founder, what was it that he missed?

3. The Biggest Hits and Biggest Misses:

• Monday: How did Entrée build such a large position in Monday over time? How did a Series A lead dropping out leading to a $1.5BN gain for Entree?
• Stripe: Entrée has now 50% of his Stripe position. Why? What is the three step process for Avi in selling positions? How does he know when to and what is the right amount?
• PillPack: Entrée made $15M from PillPack's exit. What did that teach Avi about ownership?
• Cazoo: How was Entrée the only one to make money from Cazoo? How did Entrée's sell strategy help him make millions when everyone else did not sell?