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

Lauryn Isford is the Head of Product Growth at Notion, managing Notion's product-led growth engine and self-serve business. Before Notion, she led growth at Airtable, and previously worked on growth teams including Meta, Dropbox, and Blue Bottle Coffee. Lauryn is an active angel investor and advisor supporting companies building product-led go-to-market motions.

1. From Blue Bottle to Airtable and Notion:

• How did Lauryn first make her way into the world of product and growth?
• What are 1-2 of her biggest takeaways from Dropbox, Facebook and Blue Bottle?
• What does Lauryn know now that she wishes she had known when she started?

2. What is Growth: 101:

• How does Lauryn define growth? What is it not?
• When is the right time to make your first growth hire?
• What profile should your first hire in growth be?
• What are the single biggest mistakes founders make when hiring growth teams?

3. Mastering the Onboarding Experience:

• What are the core elements of a successful onboarding experience?
• How important is time to value in onboarding today?
• What are the biggest mistakes product teams make in company onboarding?
• What is the most effective onboarding technique and workflow in PLG today?
• Why are 90% of current onboarding's done badly?

4. Making Growth work with the Rest of the Org:

• What are the single biggest barriers to growth and product working together well?
• What can leaders do to make their growth teams work well with product teams?
• How can growth teams experiment and test with product without messing up codebases?

Dave Clark is the CEO of Flexport, the global freight forwarder and logistics platform that has now raised over $2.5BN to build the category leader. Prior to Flexport, Dave began his career at Amazon in 1999 as an Operations Manager, working his way up to become the CEO of Amazon's worldwide consumer business in 2021. By the time Dave left, he was responsible for over 1 million employees. Dave spearheaded the launch of Amazon Robotics and grew the company's logistics divisions to include Amazon's own planes, trailers, and last-mile delivery vehicles through Amazon's own delivery network (which today ships more packages than FedEx and UPS). Huge thanks to Ryan Peterson for some amazing question suggestions today.

1. From Operations Manager to CEO @ Amazon:

• How did Dave Clark make his way into the world of startups with Amazon in 1999?
• What are 1-2 of his biggest lessons from spending 23 years at Amazon?
• What are 1-2 of his biggest takeaways from working alongside Jeff Bezos for 23 years?

2. How Big Leaders Make Big Decisions:

• What is Dave's decision-making framework when it comes to big decisions?
• What is the biggest decision Dave made that went wrong? How did it impact his mindset?
• How does Dave think through prioritisation as a leader today?
• What are the biggest mistakes founders make when it comes to focus?

3. How Big Leaders Hire Big Talent:

• What are 1-2 of Dave's biggest lessons on what it takes to acquire the best talent?
• Does Dave believe that people can scale with the scaling of the company?
• How does Dave think through the challenge of promoting internally vs bringing in external talent?
• Why does Dave like to hire people straight out of college? What are the benefits?

4. How Big People Deal with Big Problems: Kids, Money and Ego

• What are 1-2 of Dave's biggest lessons when it comes to parenting?
• How does Dave think about giving his kids the same hunger and ambition, when they are brought up in such affluent environments?
• How does Dave assess his own relationship to money? How has it changed over time?
• What does a truly great marriage mean to Dave? Where do so many go wrong in trying to find work-life balance?

Sheel Mohnot is a Co-Founder and General Partner @ Better Tomorrow Ventures, a $225M fund that leads rounds in pre-seed and seed-stage fintech companies globally. Sheel and Jake (his co-founder) invested for many years together before founding BTV and wrote checks into Mercury, Flexport, Ramp, and Hippo Insurance to name a few. As for Sheel, before BTV he ran 500 Fintech for close to 7 years, and before that was a founder, founding two companies, both of which were acquired.

1. VC Needs to Change:

• Why does Sheel believe that VCs should have smaller funds?
• What are the biggest misalignments between founders and VCs today?
• What are the biggest points of friction between VCs and their LPs today?

2. VC in 10 Years Time:

• Who are going to be the winners in venture in 10 years time?
• Who are going to be the losers?
• Will micro-funds be bigger or smaller as a segment of the ecosystem?
• Will solo-GPs be bigger or smaller? Were they a zero-interest rate phenomenon?

3. The Errors of a Bull Market:

• What does Sheel believe are the single biggest mistakes made by VCs between 2020-2022?
• Did Sheel take liquidity off the table in the last few years? What have been some of his biggest lessons on when to sell?
• How does Sheel evaluate the flood of capital into emerging markets in the bull market? What happens now?
• Fintech is also experiencing the same challenging time, how does Sheel assess what is happening in the fintech financing market today?

4. Building a Fund: Lessons, Mistakes and Advice Scaling to $225M:

• What are the single biggest mistakes Sheel and Jake have made in the fun scaling? How has it impacted their mindset?
• What does Sheel know now about fund management that he wishes he had known at the beginning?
• What advice does Sheel give to emerging managers today, raising their first and second funds?

Kevin Egan is the Global Head of Enterprise Sales at Atlassian and brings more than 25 years of enterprise sales experience and leadership to the company. Prior to his current role, Kevin served as the Vice President of North America Sales at both Slack and Dropbox and has held various senior sales leadership positions at Salesforce.

1. The Makings of a Truly Great Enterprise Sales Leader:

• How did Kevin first make his way into the world of enterprise sales?
• What does Kevin know now that he wishes he had known when he entered sales?
• What advice would Kevin give to a new sales leader today starting a new role?

2. The Sales Playbook:

• How does Kevin define "the sales playbook"? Does the founder have to be the one to create the sales playbook
• When is the right time to hire your first salespeople? Should they be senior or junior first?
• What are the different types of reps to hire in the early days? Should you hire two at a time?

3. PLG vs Enterprise:

• Does Kevin believe it is possible to run both PLG and enterprise playbook at the same time?
• How does one know when they are ready to scale from PLG into enterprise? What are the signs?
• What do companies need to change in the way their sales team, is structured to make the transition from PMG to enterprise sales?
• What are the single biggest mistakes Kevin sees founders make in the scaling from PLG to enterprise?

4. Hiring the Sales Team:

• What non-obvious characteristics and attitudes should we look for in sales reps?
• How does Kevin structure the hiring process for all new additions to sales and revenue teams?
• What makes good PLG sales leaders? How are they different from enterprise sales leaders?
• What questions and case studies are most revealing for you in identifying them?
• What have been some of Kevin's biggest lessons on comp structure for these early rep hires?

5. Making the Machine Work:

• How does Kevin build trust with his early sales rep hires? What works? What does not?
• How does Kevin balance hitting the quarterly revenue target with longer-term pipeline strategy?
• How does Kevin manage when a quarter is missed? What is the right approach?
• How does Kevin approach post-mortems and deal reviews? How often? What do the best entail?

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.

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?

Douwe Kiela is the CEO of Contextual AI, building the contextual language model to power the future of businesses. Last month Contextual closed a $20M funding round including Bain Capital, Sarah Guo, Elad Gil and 20VC. He is also an Adjunct Professor in Symbolic Systems at Stanford University. Previously, he was the Head of Research at Hugging Face, and before that a Research Scientist at Facebook AI Research.

1. Founding a Foundational Model Company in 2023:

• How did Douwe make his way into the world of AI and ML over a decade ago?
• What are some of his biggest lessons from his time working with Yann LeCun and Meta?
• How does Douwe's background in philosophy help him in AI today?

2. Foundational Model Providers: Challenges and Alternatives:

• What are the biggest problems with the existing foundational data models?
• Will there be one to rule them all? How does the landscape play out?
• Why does Douwe believe OpenAI's data acquisition strategy has been the best?

3. Data Models: Size and Structure:

• Why does Douwe believe it is naive to think the open approach will beat the closed approach?
• What are the biggest downsides to the open approach?
• Does the size of data model matter today? What matters more?
• How important is access to proprietary data? Are VCs naive to turn down founders due to a lack of access to proprietary data?

4. Regulation and the World Around Us:

• How does Douwe expect the regulatory landscape to play out around AI?
• Why is Europe the worst when it comes to regulation? Will this be different this time?
• How does Douwe analyse Elon's petition to pause the development of AI for 6 months?
• Do founders building AI companies have to be in the valley?

Jennifer Hyman is the Co-Founder and CEO of Rent the Runway, the world's first and largest shared designer closet. Under Jennifer's leadership, RTR has made history by being the first company to go public with a female founder/CEO, COO, and CFO. Jennifer serves on the Board of The Estée Lauder Companies and Zalando, and also is a Founding Member of the NYSE Board Advisory Council, a Member of the Women.nyc Advisory Board and a Member of the Launch with GS Advisory Council for Goldman Sachs.

1. The 14-Year Overnight Success: Scaling Rent The Runway To IPO:

• What was the a-ha founding moment for Jennifer with RTR?
• What does Jenn know now that she wishes she had known at the beginning?
• Does Jenn believe that naivete is good or not when starting a business?

2. Building the Best Team:

• What have been Jenn's single biggest lessons when it comes to acquiring the best talent?
• What have been Jenn's biggest hiring mistakes over the years?
• How does Jenn approach the interview process? Why does Jenn not focus on their professional career and achievements? What questions does she ask?
• What does Jenn believe are the single biggest mistakes founders make when building their teams?

3. Building the Business for IPO and Beyond:

• Why does Jenn wish she had run RTR as a private company in the same way she does now as a public company? How does the way you run the company differ?
• What about the unit economics of RTR suggesting it is a fundamentally better business than apparel competitors? How have their margin profiles changed over time?
• Why does Wall St not love RTR? What is required for that to change? Why does Jenn believe the street is wrong on how they analyse RTR?

4. Boards 101: Leading and Learning from Estee Lauder:

• What are Jenn's biggest lessons to founders on how to manage boards successfully?
• What have been 1-2 of Jenn's biggest lessons from being on the Estee Lauder board?
• What do the best board members do? What do the worst board members do?

Akin Babayigit is a serial entrepreneur and an active angel investor. He is currently the Founder and COO of Tripledot Studios, one of the fastest-growing mobile gaming companies in the world, which was recently valued at over $1.4BN. In just 4 years, Tripledot grew to generate several hundred million dollars per year in revenue and currently entertains over 50 million people every month. Tripledot was recently named as the #1 fastest-growing European company by FT, as well as being named as the fastest-growing Tech business in the UK, in the annual "UK Tech Awards".

Entry into the World of Startups and Gaming:

• How Akin made his way from Turkey to HBS and founding a unicorn in Tripledot?
• How did the lack of a father figure impact Akin's approach to parenting?
• What are 1-2 of Akin's biggest takeaways from his time at Facebook, Skype and King.com?
• What advice would Akin give to all new joiners at a company today?

90% of Startup Advice is Total BS:

1. BS Myth #1: "You have to be passionate about your domain". Why does Akin disagree with this? If you do not have passion for the domain, what do you have to have?
2. BS Myth #2: "You have to be solving a real problem". Why does Akin disagree with this mantra? If you are not solving a real problem, what should you be solving?
3. BS Myth #3: "When you do a startup, your life will suck for a long period of time". Why does Akin strongly disagree with this? Does it get easier over time? What does Akin advise founders to make the earlier days easier?
4. BS Myth #4: "Focus is everything. You should focus on a single thing and only do that." Why does Akin believe that focus can be dangerous? How should founders know when to pivot vs when to keep going?
5. BS Myth #5: "Mission and vision statements are so important." Why does Akin believe that the majority of mission statements are BS? Is it worth having them at all?
6. BS Myth #6: "You should hire people with domain experience." Why does Akin believe you should hire people who do not have domain experience? What does Akin look for in these candidates? What have been his biggest hiring mistakes? How has his hiring changed over time?
7. BS Myth #7: "Speed is the most important thing." Why does Akin believe that speed can be dangerous? When is it right to go fast vs go slow?
8. BS Myth #8: "Valuations matter and you should optimize." Why does Akin believe that valuations do not matter in the long run? How should founders approach the valuation discussion with this in mind?

Rob Go is a co-founder and Partner at NextView, one of the leading seed firms of the last decade with a portfolio including Attentive, Devoted Health, Whoop, and Grove Collaborative. Prior to co-founding NextView, Rob was an investor at Spark Capital and held product and product marketing roles at Ebay. He began his career as a consultant at The Parthenon Group.

1. Entry into the World of Venture:

• How a cold call from a VC firm led to Rob entering the world of venture?
• Why does Rob believe venture is a young person's game?
• What does Rob know now that he wishes he had known when started in venture?

2. Preparing Docs for a Fundraise:

• What docs should fund managers have ready before they start the raise?
• How should they structure their data room?
• Where do the majority of LPs spend their time, document-wise?
• What are the single biggest mistakes emerging managers make preparing docs for a raise?

3. Meeting Your First LPs:

• What is the best way for emerging managers to meet LPs for the first time?
• Should they send the deck before or after the meeting?
• What questions should emerging managers ask to qualify LPs in or out of a meeting?
• What are some clear early signs that a first meeting went well?

4. Closing LPs: The Tips and Tricks:

• How important is it for a fund to have an anchor?
• How much of a fund should the anchor be?
• Are there different qualities of anchor LPs?
• Should managers ever sell part of their GP or give an LP part of the carry?
• What can managers do to enforce a sense of urgency to get LPs over the line?
• What are signs that an LP will not invest in the fund without rejecting you yet?
• Should emerging managers impose a minimum check size on new LPs?

Gina Gotthilf is a Co-Founder and COO at Latitud, an a16z-backed platform supporting the next generation of iconic tech startups in Latin America through digital products, a community and fund. Previously, Gina led growth and marketing at Duolingo from 3 to 200 million users via organic strategies and was part of the executive team. She also worked on the Mike Bloomberg presidential campaign, helping oversee the creation of digital ad campaigns at a historical budget, and led growth and community for Tumblr in Latin America.

Entry into the World of Growth:

• How Gina went from working on a farm to leading growth for Tumblr in LATAM?
• What are 1-2 of Gina's biggest takeaways from her time leading growth for Duolingo?
• What does Gina know now that she wishes she had known when she entered the world of growth?

15 Top Tips and Secrets to Being Featured in the Best Publications:

• What is the best way to get in touch with journalists? What mistakes do founders have when they reach out to journalists?
• Should founders get in touch with more than one journalist at a publication?
• Should founders be explicit about the embargos they have on a story? Should they stick to them?
• Should founders be more wary of being published in a publication with a paywall?
• What materials should they send to journalists to get their attention?
• Should founders send press releases in early messages to journalists?
• How can founders control in some way what the journalist will ultimately publish?
• How long before the company wants the piece to come out, should they reach out to journalists?
• How can founders create FOMO when trying to get journalists to write their story?
• How can founders create social validity with journalists, when they are a small company?
• Once published, what should the distribution strategy look like?
• How can you get people you know to like and share content you are featured in?
• What are the top tips and tricks to get people to share content with you in?
• Should PR and Comms be an ongoing effort or static projects with news stories?
• What are the single biggest mistakes founders make in getting their company in the press?