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    Technology

    Paradigm Shift

    Candid conversations with people building the future. We discuss breakthrough moments and hard-earned insights that shaped people, products and technologies. Hosted by Ashish Kundra and Zane Salim.

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    Copyright: © 2022 Paradigm Shift

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    Latest Episodes:
    EP11: Sander Daniels, co-founder of Thumbtack, on idea exploration, key phases in building a marketplace, and his secret to effective cofounder relationships Jan 12, 2022
    Show notes

    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


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    EP10: Alanna Gregory, founder VIVE and Sr Director at Afterpay, on marketplace economics, growth marketing at Afterpay, and how NFTs could become lot more mainstream Jan 04, 2022
    Show notes

    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


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    EP9: Vrinda Gupta, founder/CEO of Sequin, on why she started a company to help women build credit, approach to building a new financial services product, and opportunities for more personalization Dec 15, 2021
    Show notes

    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!

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    EP8: Shamir Karkal, founder Bank Simple (first neobank) and Sila, on how fintech has evolved over the last decade, what he's most excited about, and predictions for the next decade Nov 14, 2021
    Show notes

    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!

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

    EP7: Finding Product-Market Fit with B2B products, with Paul Sawaya, founder Human Interest ($1b valuation) Oct 30, 2021
    Show notes

    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!

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

    EP6: Jim Brusstar, founder Treasury Prime ($31.5m Series B), on being early to fintech, how banks work under the covers, building APIs to connect banks to fintechs, and why fintech has tons of headroom to grow Sep 16, 2021
    Show notes

    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


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

    EP5: Sam Corcos, founder/CEO of Levels ($12m Seed), on lessons from early startups, why he took a year off before starting Levels, how he spent his time, and why he's building a radically open company/culture Sep 10, 2021
    Show notes

    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!

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

    EP4: Brian Ma, founder Divvy ($2b), on his early startups, building and scaling Divvy into a real estate unicorn, and investing in Southeast Asia Sep 03, 2021
    Show notes

    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!

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

    EP3: Prasanna Sankar, founder Rippling ($6.5b), on entrepreneurship, building Rippling, and crypto as the new economic engine Aug 16, 2021
    Show notes

    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!

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

    EP2: Bo Jiang, founder/CEO Lithic ($800m), on building Privacy.com and pivoting to Lithic which provides easy to use card issuing APIs to make money programmable Aug 16, 2021
    Show notes

    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

    Hit subscribe to keep up with new episodes!

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

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