In this conversation we chat about Linda’s journey from a traditional consulting career to startup rocket ships (Snap and Faire), product management, and entrepreneurship.

We start out talking about the early days at Faire and key growth unlocks that helped it quickly grow from $50m to $2.5b, and now a $12b valuation. Linda was an early product leader, and saw it grow from 14 to 300 employees. We then talk about challenges when growing that quickly and reflections on ideal culture at fast growing startups. Finally, we talk about Linda’s path towards starting Product Lessons, and building an engaged audience through her terrific writing.

We hope you enjoy this amazing episode!

Episode Highlights

1. Early career at Bain and transitioning to startups
2. Consulting as a professional bootcamp
3. Operational and product culture at Snap
4. Transitioning into PM roles at a startup
5. Faire: b2b marketplace for brands/makers and retail stores
6. What drew her to Faire ($12b co now) and early culture
7. Key growth unlocks at Faire, and building b2b virality
8. Going from as Employee 14 ($50m valuation), to 300 employees ($2.5b valuation), and 1000 employees ($12b valuation)
9. Transitioning to being a being a solo entrepreneur
10. Ideal culture at fast growing companies
11. Importance of talent density
12. Writing/creating, building product toolkit, and starting product lessons
13. Power of building email lists
14. Top Startups project to help people find great startups and jobs
15. Building an audience: find a format that works for you
16. Having a “red pill”: what are you willing to say or share that no one else is saying or sharing?
17. Mastering your own psychology
18. Superpowers, lucky break and books

Links

• Product Toolkit
• Product Lessons
• Top Startups
• Follow Linda on Twitter

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries

Click here to give feedback — it only takes a minute.

In this conversation we chat about so many key moments in Sanders journey cofounding, building and scaling Thumbtack into a $3.2b business with 900+ employees over 13 years.

We start with the founding story and weekly brainstorm calls that led to the company. We then talk about the four key phases of building a successful marketplace startup, from finding product-market fit to hyper-scaling. And finally, we talk about how Sander and his co-founders built incredible long term relationships, working together for 13+ years.

We hope you enjoy this amazing episode!

Episode Highlights

1. Growing up in DC and going to Law School
2. Two big levers to make a difference— Politics and Technology
3. Thumbtack founding— weekly phone calls brainstorming ideas for a year
4. Thumbtack today 13 years later— 900+ employees, over $500m raised, $3.2b valuation
5. How to come up with good ideas, and innovation as a deliberate process
6. Alternate ideas and names explored (like “TimeStrapped!”)
7. Marketplace liquidity as most important thing in early days
8. Early days: solved supply first, then focussed on demand for 18mos
9. Key moment in unlocking demand: early SEO insight and strategy
10. Key to growing fast: one big channel where you go super deep
11. Barriers to entry for more founders that prevent taking risk
12. How Sander overcame those barriers and how it shaped his thinking on risk
13. Challenges raising early VC based on user growth alone— 45 A-round passes
14. Four key phases: building supply, building demand, finding the right revenue model, hyper scaling
15. Challenges and frustrations during the hyper scaling phase
16. Reflection on power of focus, and also narrative/PR
17. Power of hiring exec coaches to scale as founders and a team
18. Building strong co-founder relationships: structured approach, and long term focus
19. Advice for founders and building successful long term working relationships
20. Putting on blinders and focussing on what you can control
21. Scaling as a founder and building out multiple different areas
22. Operating in your zone of genius to stay energized for 13+ years
23. Thumbtack’s culture and how they built and shaped it
24. Framework for giving/recieving feedback and turning it into an action plan for growth
25. Reflections on Thumbtacks superpowers and shadows of those strengths
26. Book recommendation: Design Your Life
27. New projects: (1) Scaled- bringing innovation to recruiting (2) New mobile dog grooming business that can train and up level anyone to earn $100k+
28. Sander’s super power, lucky breaks, and book recommendations

Links

• Start using Thumbtack to find local professionals for pretty much anything
• Hire People, Finance, Legal talent with Scaled
• Follow Sander @sanderdaniels

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries

Click here to give feedback — it only takes a minute.

In this conversation with Alanna we talked about pivotal moments in Alanna’s journey from working on emerging markets research on Wall St, to founding a YC backed marketplace startup, to growth marketing leader at Afterpay. Alanna has a broad and unique perspective on startups, fintech and crypto, and in this conversation we cover a wide range of topics across all three.
 

Episode Highlights

1. Starting her career on Wall St during the 2008 financial crisis
2. Culture working in finance vs tech
3. Founding VIVE — what drove her to marketplaces
4. Vision to build a marketplace that helps salons acquire customers
5. Explosive early demand — 14,000 customer waitlist
6. Challenging unit economics — trade-offs between unlimited usage and credit system
7. Explorations — marketplace vs SaaS vs bundling CPG products
8. Key learning — PMF is about finding and meeting demand in a scalable way, unit economics and margins important even at early stages
9. Joining AfterPay to lead growth marketing for engagement and retention
10. Approach towards consumer vs merchant, and checkout product vs standalone app
11. Thoughts on fintech and potential risks in the system
12. How startups build/validate a new lending product as a startup and risks to manage
13. Thoughts on DeFi and NFTs — both quickly going more and more mainstream
14. How NFTs and e-commerce could merge and enable new products and marketing levers
15. Thoughts on what might happen if interest rates go up — mental model on opportunities if markets retreat or become more volatile
16. Super powers on spotting talent and hiring, people who have her a break, and books

Links

• Follow Alanna @alannaeve on Twitter

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries

Click here to give feedback — it only takes a minute.

Summary

In this conversation with Vrinda we cover a wide range of topics including how the current credit system works, why women are more likely to have negative credit experiences, and how Sequin solves that inequity gap with a new debit card for women that helps build credit. We also talk about the process of launching a new card based product at a bank vs. a startup, and both opportunities and challenges to innovate in the space.

Episode Highlights

1. Working on Chase Sapphire card at Visa and getting rejected for it
2. Challenge of credit: needing credit to get credit
3. How credit score gets calculated and factors contributing to bias
4. Why women get rejected for a credit card more often than men
5. Speed of launching a card at a bank vs. as a startup
6. Considerations in designing a new card
7. Building Sequin as a debit card that builds credit
8. How to think about benefits as a fintech startup vs at scale
9. Surprising insights: huge appetite for knowledge, community and card design
10. Approach to education and community building as a fintech
11. Vision for Sequin: full suite of credit products for women across every life stage
12. Going from fintech idea to prototype/MVP as a non-technical founder
13. Insight: importance of credit utilization to build credit
14. Moving fast without breaking anything as a fintech
15. Early next year: re-launching the debit card that builds launch with rewards partners
16. Opportunity to create hyper personalized products that grow with customers
17. Superpowers: capacity for empathy and how she's built it, and ability to pattern match
18. People who gave Vrinda a break, and book recommendations

Links

• Read more about Sequin ($5.7m Seed) and get the card: https://www.sequincard.com/
• Follow Vrinda @vrinda_tweet

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries

Click here to give feedback — it only takes a minute.

Summary:

Conversation with Shamir Karkal, co-founder of Sila. Prior to Sila, he was co-founder of Bank Simple, which was the first US neobank and early fintech pioneer. For many it was one of the most exciting and groundbreaking products of the last decade. We talk about the Bank Simple story, banking and fintech landscape, and his new company Sila. Sila makes it easy for any business to program money through APIs for digital wallets, linked accounts, ACH, money storing, transferring and payouts.

Episode Highlights:

1. Career path from software engineer to consultant at McKinsey with financial services clients
2. Founding story and vision for Bank Simple — first US neobank, founded in a Brooklyn basement
3. Why starting a bank in 2009 was crazy, and how the landscape evolved after the 2008 financial crisis
4. Inventing the modern fintech bank partnership model and path to market with a simpler bank that replaced retail branches with software and no-fees
5. Story behind selling to BBVA for $117m after raising only $20m
6. Getting excited about building fintech platforms to make access to banking infra easier, and founding Sila
7. How Sila makes it easy for any business to program money through APIs for digital wallets, linked accounts, ACH, money storing, transferring and payouts
8. History of regulatory landscape around getting a full banking charter — 100s a year before 2008 to just a handful in the following decade, and how its becoming more feasible again
9. Pros and cons to having a banking charter— ability to lend FDIC insured deposits and fully leverage the "3, 6, 3" business model
10. How cyclical nature of credit industry and credit crunches makes stable FDIC deposits high-value for the lending business model of banks
11. Bank Simple's business model, unit economics and strong early growth
12. Activation and direct deposit as a key product lever for newer neobanks
13. Looking forward, why global financial services industry is exciting— $17T annual revenue industry, 30x larger than $600b global advertising industry (out of ~$100T global GDP)
14. Opportunity for fintech to go from 1% market share to 10% this decade
15. Prediction: fintech and crypto in 2030 could be as big as all of tech in 2020, with few $1T+, few dozen $100B+, and 100s of $1B+ companies
16. Crypto doesn’t change underlying trends but might accelerate through faster/easier permissionless innovation on a global scale
17. Regulators can’t control on chain work but can regulate on/off ramps and how Sila enables on/off ramps and connectivity between crypto and traditional banking through flexible APIs

Links:

• Read more about Sila: https://silamoney.com/
• Follow Shamir on Twitter: https://twitter.com/shamir_k

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries

Click here to give feedback — it only takes a minute.

Summary:

Conversation with Paul Sawaya, co-founder of Human Interest, $1b company that makes it easy for SMBs to provide 401k savings plans to their employees, and helps employees save for their retirement.

We cover so many interesting topics in this conversation across the Human Interest story, numerous lessons learnt, and technologies he's most excited about for the future.

Episode Highlights:

1. Early experiences like building an FB app at Bloomberg
2. Interviewing with Emmett Shear to interview at Justin.TV
3. How big company vs tiny startup experience made him want to start a company
4. Spending 2 years exploring problems and ideas
5. Challenges and lessons from wandering the wilderness
6. Key lesson: focussing on problems first before jumping into futuristic projects
7. Got excited about solving 401k access problems which led to Human Interest
8. Only 20% small companies offered 401ks due to setup, admin and cost challenges
9. Product innovation: automating operational work to lower cost structures and expand access
10. Building on top of back-office solutions to learn/move fast, then moving in-house
11. How they moved fast to get early customers for feedback and validating demand
12. How to spend time during exploration/sabbatical: establish a routine and talk to lots of people
13. Approaching GTM through an effective partnership and integration strategy
14. Cleaning up some shady 401k practices by offering better, sustainable solutions
15. Transitioning out of day to day Human Interest work to spend time with early stage startups
16. Exploring new ideas for his new project and things he's excited about
17. Exciting breakthroughs other people might be under-appreciating: Web Assembly to run high intensity server side compute locally in the browser, and AI to reimagine user interfaces
18. Prototyping to explore and learn new things
19. Ability to enter ambiguous, messy situations and find a path forward
20. People who gave him an early break that he is grateful for
21. Power of developing personal values as a guiding light

Links:

• Read more about Human Interest: https://humaninterest.com/
• Follow Paul on Twitter: https://twitter.com/automin

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries

Click here to give feedback — it only takes a minute.

Conversation with Jim Brusstar, co-founder of Treasury Prime, which is building APIs to connect a network of banks to fintechs. They make it easy for fintechs to partner with the right bank, and reduce the time to market for a neo bank or embedded banking product from years to months.

We cover so many interesting topics in this conversation — starting with being early at Sidecar and lessons learnt from competing with Uber and Lyft, being early to fintech with Standard Treasury which built banking APIs and sold to Silicon Valley Bank, how banks work under the covers, and why he decided to found Treasury Prime (with same mission as Standard Treasury).

We also talk about why Jim is excited about fintech and how most people underestimate how early we are in fintech overall— with lots of headroom for innovation and growth.

Episode Highlights:

1. Why Jim decided to start a company
2. Early days at Sidecar — and inventing ride sharing
3. Sidecar — getting out executed by Lyft and Uber
4. Thanksgiving 2012 — cease and desist to all ride sharing companies
5. Early fintech — building "Banking in a box" APIs at Standard Treasury and being too early
6. Acquisition by Silicon Valley Bank and how banks work under the covers
7. Banking business model (incentives) — buying deposits and selling loans
8. Starting Treasury Prime — with same mission as Standard Treasury
9. Building a network of banks — infra layer with modern APIs + match Fintechs with right bank
10. How infra layers and APIs unlock innovation — reducing time to market from years to months
11. Use cases and business models on top of Banking APIs
12. Benefits of using Treasury Prime to connect with a network of banks
13. Why Fintech is super early — less than 1% of all deposits today and where next gen will bank
14. Thoughts on crypto use cases — international remittences and programatic settlement

Links:

• Read more about Treasury Prime Use Cases and Banking APIs
• Follow Jim on Twitter at @JimBru

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries

Click here to give feedback — it only takes a minute.

Conversation with Sam Corcos, CEO of Levels health, who is a prolific serial entrepreneur and building one of the most exciting companies in healthcare today. Levels is a groundbreaking product that helps people track their blood glucose in real-time to understand and improve their metabolic health.

We talk about key lessons Sam learnt from his first few startups, why he took a year off before starting levels, how he honed in on the idea for Levels, his approach towards building a radically open company, and areas he's most excited about for the next 5-10 years.

This episode is packed with real insight into what it's like to be a serial founder, and full of actionable advice on how to explore ideas, find purpose, and work hard without burning out.

Episode Highlights:

1. Early startups and nomadic adventures
2. Building a high-trust culture that supports risk taking
3. Thoughts on hiring as a matching problem
4. Why (and how) he's building a radically open company
5. Biggest lessons from Sightline Maps and CarDash
6. Building effective co-founder / interpersonal relationships
7. Sam's framework for choosing what problems to work on
8. Why he took a year off before Levels and how he structured his time
9. Approach to network management and maintenance
10. Approach to time management while exploring ideas
11. How he converged on the Levels idea and product
12. What Sam's excited about for the next 5-10 years
13. Thoughts on synthetic biology
14. Sam's superpowers and how he's honed them

Links:

• Check out Levels' product and unlock your metabolic health
• Follow Sam on Twitter at @SamCorcos
• Read more about why Levels is building in public
• Levels' internal company podcast

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries

Click here to give feedback — it only takes a minute.

Conversation with Brian Ma - who interned at Zillow when it was 15 people, joined as employee #32, and went on to become a prolific serial entrepreneur. We talk about his entrepreneurial journey founding Decide.com, Weave, Divvy Homes ($2b unicorn), and most recently, a SE Asia focused Seed fund and accelerator.

Some highlights from the conversation include how he skipped high school, why he joined Zillow, his first few companies, going on a "vision quest", his approach to exploring new ideas, the early days at Divvy Homes, and his recent fund and why he is excited about investing in South East Asia.

Episode Highlights:

1. Brian's life mission and how it led him into startups
2. Skipping high school and doing early-entry and Univ of Washington
3. Interning at Zillow when it was 15 people and being an early employee
4. First company: Decide.com
5. Moving to Silicon Valley, starting Weave, and YC experience
6. Going on a vision quest
7. Approach to exploring new ideas
8. Working with Max Levchin to incubate Divvy Homes
9. Early days and finding PMF at Divvy Homes (now $2b unicorn)
10. Why he started Iterative.VC and is excited to invest in SE Asia

Links:

• Follow Brian on Twitter at @zealoustiger
• Read more about Divvy Homes and how rent-to-own works
• If you're a startup in South East Asia, apply to the next cohort of Iterative.VC

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries

Click here to give feedback — it only takes a minute.

Conversation with Prasanna Sankar - whose most recent company, Rippling, went from zero to $1.35b valuation in less than 4yrs. We talk about his experiences working on startups for over 10 years, finding and scaling success at Rippling, and why he believes crypto will be a transformative new economic engine.   

Episode Highlights:

1. Getting started as a programmer in high school
2. Approach to building from first principles and becoming the top ranked coder in India
3. Moving from Microsoft Bing team to Silicon Valley and pitching to Paul Graham
4. Building LikeALittle - hyper-growth phase, passing on M&A, eventual crash and burnout
5. Joining Zenefits and the visionary genius of Parker Conrad
6. Founding Rippling - clear and ambitious vision requiring a large up-front build
7. Path to $1.35b valuation in under 4 years, leading to hyper growth and scaling phase
8. The blockchain movement and why it could be the next big thing
9. Thoughts on crypto use cases and framework for how adoption will grow over time 
10. Ethereum as the gateway into crypto-native activities 
11. Exciting infrastructure being built today - faster Ethereum, and high speed bridges between chains
12. Why blockchain will be the economic engine for the future, and how it allows creators to maximize wealth creation
13. Thoughts on planned move from the US to Singapore which is becoming the "crypto capital of the world"
14. Recommended reading: Tendermint white paper on Consensus without Mining

Links:

• Follow Prasanna on Twitter at @myPrasanna,  check out his terrific blog, and his AngelList fund
• For more of Prasanna's thoughts on crypto/blockchain, check out his blog post on Building a Trillion Dollar Crypto Business, and his talk on Blockchain- The New Steam Engine

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries

Click here to give feedback — it only takes a minute.