Paradigm Shift

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

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

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

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

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

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

Conversation with Bo Jiang - founder and CEO of Lithic, which offers an API for card issuing. We talk about Bo's incredible journey starting out as a consumer focussed company (Privacy.com), and pivoting to Lithic, which is an easy to use API for card issuing. 

Today, Lithic is one of the fastest growing company in Fintech and recently announced a Series C at an $800m valuation. In this conversation, we focus on the early days and pivotal moments in Bo's journey. 

Episode Highlights:

1. Growing up in the midwest
2. How Bo got started building products
3. Story and insight that led to Privacy.com
4. Challenges building on a legacy processor
5. Anatomy of a card transaction - acceptance vs issuance
6. Why they built their own infrastructure for issuance
7. Lightbulb moment to pivot from Privacy.com to Lithic
8. Programmable money and new use cases the Lithic API enables
9. Impact of Covid - metrics and remote work
10. Thoughts and reflections on crypto 

Links:

• Follow Bo on Twitter @bolingj
• Read this terrific analysis on Not Boring to learn more about Lithic
• Check out the Lithic website to explore use cases and get started with the API, and Privacy.com for personal payments
• Lithic is growing fast and hiring across almost all areas -- explore their open opportunities

Interview with Jonathan Wegener -- one of the most innovative product thinkers we know. We talk about his experience founding Timehop, working on Evan Spiegel's design team at Snap, and what he's working on next ("active" audio-based products). 

Episode Highlights:

1. How Jonathan got started building products
2. How he got into startups and started building online businesses
3. How Timehop started at a Foursquare hackathon
4. Timehop early traction and explosive growth
5. Lessons from raising Series A and hyper growth phase
6. Facebook launches competing "on this day" product
7. Timehop's evolution and new advertising business
8. Joining Evan's design team at Snap
9. Snap's vision driven design culture "Willy Wonka chocolate factory of tech"
10. What he's working on now-- Active Auditory Experiences
11. Framework for Active Audio (Eg: Detour), Passive Audio (Eg: Music), Active Video (Eg: Gaming) and Passive Video (Eg: Netflix)
12. How and why Active Audio experiences could be a big new category

Links:

• Follow Jonathan on Twitter at @JWegener
• Download his latest app GoGoGames! to experience active audio adventures