Paradigm Shift

Ashish Kundra and Zane Salim

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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EP28: Building an open source powered product and company, with AppSmith Co-Founder/CEO Abhishek Nayak
Jul 20 2022
EP28: Building an open source powered product and company, with AppSmith Co-Founder/CEO Abhishek Nayak
Abhishek is the co-founder and CEO of AppSmith, which is a low-code tool that helps developers build dashboards and admin panels very quickly. AppSmith has raised over $50M from investors like Accel, Bessemer, Insight and Prasanna Sankar (previously on the pod!).In this conversation we primarily explore how Abhishek is building AppSmith with the open source community as a core part of the product, business model and long term strategy. We also talk about Abhishek’s incredible journey (and lessons) as a serial entrepreneur, how the Indian startup ecosystem has evolved over the last 10+ years, and the key drivers behind the trend of Indian startups building for the world.In this episode we discuss:Lessons from serial entrepreneurship and journey to founding AppSmith How did you get into building things?What were the most impactful learnings from your early startups?What is AppSmith and what led you to founding the company?AppSmith and building an open source powered company How did you evaluate whether to build an open source company? And whether open source could be both an advantage and a viable strategy for AppSmith?What are some of AppSmith’s biggest differentiators vs other no-code internal tool products in market today?How did you approach getting your first customer? How did you evaluate early product market fit for the open source product/project?What were the biggest risks you were focused on mitigating early on and how did you approach it?What have you experienced as being the biggest advantages of building an open source product/company?What is your current scale and traction about 20 mos after launch?Growth and monetization for an open source project What does the open source flywheel look like and which levers are you most focused on to drive adoption and keep improving the product?Where do you focus your marketing and growth efforts for an open source company?Why do people choose you over alternatives? How do customers and buyers evaluate the pros/cons of the open source nature of your product?In the context of your open source approach, what is your business model and how do you think about your monetization strategy?What’s your long term vision for AppSmith and what’s your approach to getting there?What has been the big differentiator between open source projects that have had great monetization vs ones that have struggled with monetization?Indian startup ecosystem From your vantage point, what have been some big inflection points from the last 10+ years that have led to the thriving Indian startup ecosystem?What do you think is driving the trend of Indian startups building for the rest of the world?What are some of the advantages you see to building world class products in India?Closeout questions What is the most challenging or difficult feedback you’ve received and how have you incorporated it going forward?What are your superpowers that you find yourself leaning on often?What’s something you believe that would surprise most people?LinksLearn more about AppSmithFollow Abhishek and AppSmith on TwitterHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute
EP28: Building an open source powered product and company, with AppSmith Co-Founder/CEO Abhishek Nayak
Jul 20 2022
EP28: Building an open source powered product and company, with AppSmith Co-Founder/CEO Abhishek Nayak
Abhishek is the co-founder and CEO of AppSmith, which is a low-code tool that helps developers build dashboards and admin panels very quickly. AppSmith has raised over $50M from investors like Accel, Bessemer, Insight and Prasanna Sankar (previously on the pod!).In this conversation we primarily explore how Abhishek is building AppSmith with the open source community as a core part of the product, business model and long term strategy. We also talk about Abhishek’s incredible journey (and lessons) as a serial entrepreneur, how the Indian startup ecosystem has evolved over the last 10+ years, and the key drivers behind the trend of Indian startups building for the world.In this episode we discuss:Lessons from serial entrepreneurship and journey to founding AppSmith How did you get into building things?What were the most impactful learnings from your early startups?What is AppSmith and what led you to founding the company?AppSmith and building an open source powered company How did you evaluate whether to build an open source company? And whether open source could be both an advantage and a viable strategy for AppSmith?What are some of AppSmith’s biggest differentiators vs other no-code internal tool products in market today?How did you approach getting your first customer? How did you evaluate early product market fit for the open source product/project?What were the biggest risks you were focused on mitigating early on and how did you approach it?What have you experienced as being the biggest advantages of building an open source product/company?What is your current scale and traction about 20 mos after launch?Growth and monetization for an open source project What does the open source flywheel look like and which levers are you most focused on to drive adoption and keep improving the product?Where do you focus your marketing and growth efforts for an open source company?Why do people choose you over alternatives? How do customers and buyers evaluate the pros/cons of the open source nature of your product?In the context of your open source approach, what is your business model and how do you think about your monetization strategy?What’s your long term vision for AppSmith and what’s your approach to getting there?What has been the big differentiator between open source projects that have had great monetization vs ones that have struggled with monetization?Indian startup ecosystem From your vantage point, what have been some big inflection points from the last 10+ years that have led to the thriving Indian startup ecosystem?What do you think is driving the trend of Indian startups building for the rest of the world?What are some of the advantages you see to building world class products in India?Closeout questions What is the most challenging or difficult feedback you’ve received and how have you incorporated it going forward?What are your superpowers that you find yourself leaning on often?What’s something you believe that would surprise most people?LinksLearn more about AppSmithFollow Abhishek and AppSmith on TwitterHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute
EP27: Building crypto products for mainstream users, with CoinList Co-Founder and Eco Co-Founder/CEO Andy Bromberg
Jul 11 2022
EP27: Building crypto products for mainstream users, with CoinList Co-Founder and Eco Co-Founder/CEO Andy Bromberg
Andy is a serial entrepreneur and CEO of Eco a new kind of wallet to spend, send and save money. It combines traditional banking rails with crypto rails to deliver a new kind of experience that creates more value for customers in an easy to access way. Before Eco Andy was a co-founder at CoinList which is another very successful crypto project.In this conversation we talk about the founding stories behind both CoinList and Eco. We discuss Andy’s lessons from navigating the last crypto winter. And we discuss Andy’s approach to building Eco into a mainstream crypto-based product that competes with traditional retail banking.In this episode we discuss:Early career building things How did you get stated building things?What are some memorable lessons from the Stanford Bitcoin Group?CoinList and the early ICO token sales wave What was the founding story for CoinList?How did you approach the decision on whether to spinout CoinList from AngelList?Who was the first customer (Filecoin) for CoinList and how did you scale from there (Eg: Blockstack)?What were the biggest challenges running an early crypto company?How did you approach operating the company during the last crypto winter?What advice do you have for founders grappling with the current crypto winter/pullback?What was the strategy behind the large $100M Series A fundraise?What were the new services/business lines you added and how did you approach that?How did you nurture the marketplace and network effect dynamic at CoinList?Founding and leading Eco What was the founding story behind Eco and what led you joining the team?How did you build conviction on the idea and opportunity behind Eco?What were the early services and features that really resonated with consumers?How did you approach building for mainstream consumers / normies?How have you gotten people to switch from traditional banks to Eco?What is the biggest growth bottleneck (potential unlock) for Eco’s next phase of growth?What is our approach to building during the current downturn?Why should someone sign up for Eco today?What is your vision for the product and company?How do the economics for rewards and yield work in the current market context?How do you think about CAC and lifetime value of a customer?Closeout questions What is the most challenging/difficult feedback you’ve received — how have you processed it and incorporated it going forward?What are your superpowers that you find yourself leaning on often?LinksLearn more about EcoFollow Andy and Eco on TwitterHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute
EP26: Reimagining healthcare from first principles, with Forward Founder/CEO Adrian Aoun
Jun 19 2022
EP26: Reimagining healthcare from first principles, with Forward Founder/CEO Adrian Aoun
Adrian is a serial entrepreneur and currently Founder/CEO of Forward. Forward is a healthcare startup that provides a membership-based healthcare system. Forward is redesigning the way healthcare is delivered using cutting edge technology that has long been neglected such as sensors, mobile, and AI.Before Forward Adrian founded AI startup Wavii which was acquired by Google, where he subsequently led Special Projects for the entire company. In this episode we dive into Adrian’s entrepreneurial journey and how Forward is redefining healthcare from first principles.In this episode we discuss:Wavii and early journey as an entrepreneur What led you into an entrepreneurial path?What was Wavii and how did it apply AI?How did you end up getting acquired by Google?How did you approach AI at Google post acquisition?Leading Special Projects at Google How did you end up working with Larry Page on Special Projects at Google?How did you approach structuring and creating the various Alphabet companies?How did you approach problems, prioritize opportunities and measure impact?What was working with Larry Page like and what were his greatest strengths?How did you apply first principles thinking when starting new projects at Google?Why is Forward not an Alphabet company?Reimagining healthcare with Forward What is forwards goal and what led you to founding the company?What were some of the principles that gave you conviction in building D2C healthcare?What is your perspective on competing with incumbent business models?What is your vision for Forward and shifting healthcare from inflationary to deflationary?Path to Product Market Fit and Scaling Forward What was your path to Product Market Fit and proving out the D2C business model?How did you maintain conviction and push back on calls to pivot in the early days?How did you figure out how to tell your story and start driving growth?What does your current scale look like and what have been the hardest parts to scale?From a consumer’s perspective, why should someone sign up for Forward?What do the economics look and how do you make them work without taking insurance?How do you supercharge doctors and build tools to turn healthcare into a product?What are the segments where you’re seeing the best fit today and expanding from?Closeout questions What are your superpowers that you find yourself leaning on often?What is the most challenging/difficult feedback you’ve received — how have you processed it and incorporated it going forward?Who’s the most talented person you’ve worked with & what do you respect most about them?LinksLearn more about ForwardFollow Adrian and Forward on TwitterHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute
EP25: Founding and scaling a logistics unicorn, with ShipBob Co-Founder/CEO Dhruv Saxena
Jun 11 2022
EP25: Founding and scaling a logistics unicorn, with ShipBob Co-Founder/CEO Dhruv Saxena
Dhruv is the Co-Founder/CEO of ShipBob, the leading global omni-fulfillment platform designed to provide small and medium-sized businesses access to best-in-class supply chain and fulfillment capabilities.Dhruv started ShipBob in his Chicago apartment in 2014, and has scaled it today to over 7,000 e-commerce brands, with fulfillment centers around the world. They’ve raised $300m+ and have achieved a $1B valuation.In this episode we discuss:Going from an Electrical Engineering PhD to building things How did you end up building things?What were some early ideas and products you tested?What led you to the problem you’re solving with ShipBob?How did you build conviction to quit your job and start ShipBob?Founding ShipBob and finding Product Market Fit What was the problem you were trying to solve?What was your initial solution?How does third party logistics work and what was new about ShipBob?How did you solution evolve over time?How important was timing with e-commerce wave and how did you approach competition?What were some of the biggest inflection points that drive growth?When did you know you had strong product market fit?Approach to blitz-scaling How did you approach scaling an operations heavy business?What was your approach to getting the unit economics right before scaling?How did you approach fundraising and finding the right partners for your business?How did you approach blitz-scaling and how did you evolve your role as a leader?What advice do you have for founders making the transition from pre to post PMF mode?Logistics market and recent disruptions What are some of the challenges you and your customers are facing?What have been some of the recent headwinds and tailwinds for e-commerce brands?Closeout questions What is the most challenging/difficult feedback you’ve received — how have you processed it and incorporated it going forward?What are you optimizing for at this point in your career and how has that evolved over time?What are your superpowers that you find yourself leaning on often?LinksLearn more about ShipBobFollow ShipBob on TwitterHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute
EP24: Market landscape and opportunities in the Indian software ecosystem, with Nikhil Sachdev, Managing Director at Insight Partners focused on software, fintech and crypto
Jun 7 2022
EP24: Market landscape and opportunities in the Indian software ecosystem, with Nikhil Sachdev, Managing Director at Insight Partners focused on software, fintech and crypto
Nikhil is a managing director at Insight Partners, where he invests in software, fintech, and crypto companies. In this conversation we talk about the recent market corrections, investment landscape in the Indian startup ecosystem, and some of the opportunity areas Nikhil is most excited about across software/SaaS, fintech and crypto.In this episode we discuss:Market context and Insight Partners as a fund What’s your perspective on the current market backdrop?What are the areas Insight Partners is most focused on?What are you seeing behind the scenes in terms of fundraising activity?How has your advice/guidance for companies changed vs 3mos ago?What are some asymmetric opportunities for founders when fundraising gets harder?What are some efficiency metrics that you find yourself focusing more on?Opportunities areas and trends in the Indian market, fintech, and crypto What’s your “why now” for the Indian startup market?What are some recent investments you’ve made and what was most exciting to you?What does the earliest stage of funding look like in the Indian startup market?How do you think about exit scenarios and exit valuations in the Indian market?What’s your take on Indian fintech and opportunity areas?What are your thoughts on long term monetization in the Indian market?What types of crypto opportunities have you been focused on?Closeout questions What are some of your superpowers that you’ve learnt to rely on often?What is something you believe that might surprise most people?What content have you consumed recently that has made an impact?LinksFollow Nikhil on TwitterLearn more about Insight PartnersHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute
EP23: Building in public and the future of AI powered creative tools, with Paul Yacoubian, founder/CEO of Copy.AI
May 23 2022
EP23: Building in public and the future of AI powered creative tools, with Paul Yacoubian, founder/CEO of Copy.AI
Paul Yacoubian is the founder/CEO of Copy.AI. CopyAI is building AI-powered tools that help users automatically generate marketing copy in seconds, and has over 1M registered users.Paul is an extremely positive and inspiring presence on twitter and has mastered the art of building in public. In this conversation we talk about Copy.AI, Paul’s approach to building in public, and the future of AI powered tools.In this episode we discuss:Building in public How did you get started building in public?What principles guide your online content?What have been the benefits of building online?How has it helped you get early adopters and investors?How do you approach how much time to spend on twitter?What advice do you have for someone getting started building in public?Copy.AI and future of AI powered tools What is copy AI and what is the long term vision?How do people use Copy AI to generate copy and ideas?How do you make AI better at writing copy?What are some really popular use cases?How much of the AI is off-the-shelf vs your own models?How unique and defensible is the AI in workflow tools?How do users make the product better in workflow tools?What channels have worked best to acquire your 1M registered users?What has engagement, retention and monetization looked like?What do you think the future of AI powered creative tools looks like?Closeout questions Who is the most talented person you have worked with and why?What are some superpowers you have identified in yourself and like to lean on?LinksFollow Paul on TwitterCheck out Copy.AIHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute
EP22: Lessons from building world class teams at Carta and DoorDash, with Nolan Church, founder/CEO of Continuum, ex-Chief People Officer at Carta, ex-Head of Talent at DoorDash
May 15 2022
EP22: Lessons from building world class teams at Carta and DoorDash, with Nolan Church, founder/CEO of Continuum, ex-Chief People Officer at Carta, ex-Head of Talent at DoorDash
Nolan is one of the best HR leaders in the world for high growth startups. He’s currently the Founder/CEO at Continuum, which is a talent marketplace that helps startups hire the best people for key functional needs, and helps executives work with multiple companies at once.Before that he was the Chief People Officer at Carta helping it grow to a $10b valuation, Head of Talent at DoorDash from early days of 50 employees to 800+ employees, and a recruiter at Google helping scale a new org from zero to 80 engineers.Thanks to Ashley Davis and Jessica Stolbach for contributing some great questions.In this episode we discuss:Early career and landing at Google How did you go from being a collegiate baseball player to working at Google?What did you learn at Google based on how they approached recruiting?How did Google approach Hiring Committee and what did you learn from it?What did the recruiting funnel look like at Google vs startups later in your career?What did speed of hiring look like at Google vs Facebook, startups, etc?Leading recruiting for DoorDash during hyper growth from 50 to 800+ How did you end up at DoorDash and what was the scale like? h/t Kym Lee!You’ve said Tony is the best recruiter in the world. What makes him so great?What were you optimizing for when you moved to DoorDash and why did you pick them?What were the challenges recruiting and how did you approach it?How did you maintain and raise the hiring bar while scaling quickly?How did you get hiring managers to own sourcing and recruiting outcomes?What KPIs and funnel metrics were you focused on each month/quarter?How did you hire people better than you? How did you help people grow?Leading the HR function at Carta as CPO What led you to Carta? What was the state of the company when you got there?What was the nature of the network effect at Carta that fueled the business?What are your observations on some of the problems with equity today?What are some trends you’ve seen in the talent and equity market?Founding story and vision for Continuum What is Continuum and what problems are you solving?What are you hearing from companies and execs on fractional opportunities?What is your vision for Continuum?What has been the most humbling part of being a first-time founder?Recruiting and HR at startups What is your HR advice for early-stage founders?How should founders think about HR strategically?When should a startup hire their first recruiter?What do you look for when hiring recruiters?How do you think about the value of an advisor?What makes someone a great recruiter?Closeout questions What is the most difficult feedback you’ve received?What are you optimizing for at this point in your career and how has that evolved?What are some of your superpowers that you find yourself leaning on often?LinksFollow Nolan on TwitterRead Nolan’s thread on he helped DoorDash grow from 50 to 800+ employeesCheck out Continuum— to hire an exec or join as an execHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute
EP21: Building and growing a community of over 15M Indian women, with Sairee Chahal, founder/CEO of Sheroes and Mahila Money
May 2 2022
EP21: Building and growing a community of over 15M Indian women, with Sairee Chahal, founder/CEO of Sheroes and Mahila Money
Sairee is a serial entrepreneur and Founder/CEO or Sheroes. Sheroes is a social network with over 15M women. It helps empower them with a broad set of tools, community, jobs, entrepreneurial opportunities and financial services. It’s profitable and has quickly grown to several million in top line revenue. Sairee is also the founder of Mahila Money and serves on the board of PayTM Payments Bank.In this episode we discuss:Founding and growing Sheroes to a profitable community of 15M women What led you to tech entrepreneurship?What led you to found Sheroes?What problems do you solve for women?What are gender rankings and how do they work?How are users using Sheroes today?How does Sheroes unlock more opportunities for women?How did you grow to a 15M community?How do you build and maintain trust in the product?How do you make money and what’s your current revenue? Fintech and startup ecosystem in India What led you to found Mahila Money— banking for women?What is the current state of fintech in India?Where do you see the biggest fintech opportunities in India?Closeout questions Who is the most talented person you have worked with and why?What are some things you believe that would surprise most people?What are some of your superpowers that you’ve learnt to lean on often?LinksFollow Sairee on TwitterCheck out Sheroes and Mahila MoneyHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute.
EP20: DeFi and Yield Farming deep dive, with Kedric Van de Carr, serial entrepreneur, DeFi investor and co-founder of DeFi Masterclass
Apr 19 2022
EP20: DeFi and Yield Farming deep dive, with Kedric Van de Carr, serial entrepreneur, DeFi investor and co-founder of DeFi Masterclass
Kedric is a serial entrepreneur who co-founded and teaches the DeFi Masterclass, a hands-on workshop that has helped 100s onboard into the world of DeFi, learn how to research crypto opportunities, and make a passive income.Before DeFi masterclass Kedric was co-founder of Unblockable which builds crypto and NFT/sports prediction games. He also co-founded performance marketing agency Playbook Media, and was Chief Business Officer at Exitround, a marketplace for private company M&A.In this episode we discuss:The hook that got Kedric to go down the DeFi rabbit hole What was your first DeFi experience and aha moment?What led you from skepticism to curiosity to excitement?What DeFi is and how does it work?How to understand risk, returns and yields?How DeFi yield farming works and generates passive income How does DeFi work in a decentralized way and eliminate middlemen?How do transactions between two assets or parties happen in DeFi?How does decentralized finance increase automation, lower costs, and increase access to yield/revenue from automated market making?What is driving yields and rates of return on assets in DeFi?How to identify, research and evaluate yield opportunities/risks What are the different ways to invest and earn a return in DeFi?How do you research opportunities and filter signal from noise?How do you evaluate potential based on narrative/speculation, and cashflow/DCF?What are some examples of crypto projects with low DCF valuation right now?How do find information/data to analyze yield farming opportunities?What are the categories of risks a crypto investor should bear in mind?What is your framework for evaluating risk, returns and constructing portfolios?What are typical returns for low risk, med risk and high-risk opportunities?How to earn 32.9% ROI per year through a simple risk management portfolio framework?How do you think about counter-party risk for stable coins?Outlook on future of DeFi and yields What are the biggest barriers to more trust and adoption of DeFi?What is your take on government oversight and the regulatory landscape?Whats your outlook on yield farming opportunities in the current crypto landscape?Closing questions Who is the most talented person you have ever worked with?What is something you believe that would surprise most people?What superpowers do you like to lean on day to day?Who are some people that have helped you along the way?LinksFollow Kedric on TwitterCheck out DeFi Masterclass and sign up for the hands-on workshop! We couldn’t recommend it more highly. We made our class fee back in just a few months.Learn more from Kedric on yield farming portfolio construction to earn best in industry returns while managing risk and how DeFi can reduce the wealth gapHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute
EP19: Building and scaling nationwide virtual primary care, with Sean Mehra, founder and CEO of HealthTap
Apr 6 2022
EP19: Building and scaling nationwide virtual primary care, with Sean Mehra, founder and CEO of HealthTap
Sean is founder and CEO of HealthTap which makes primary care affordable and easy to access for all Americans. In this episode we discuss:HealthTap’s virtual primary care clinic Affordable solution for all Americans regardless of whether they have insuranceHow it works from user experience to business modelTypes of conditions and issues that can be treated through primary careHow HealthTap approaches different use cases and care scenariosBuilding a healthcare product and company How to get early tractionImportance of patience and resilienceMaximizing luck surface areaBeing early to telehealth and growing with the marketImpact of pandemic to tele-healthExploring multiple business models in healthcare Connecting consumers online with 90k physiciansBuilding a trusted Doctor powered UGC powerhouseLeveraging UGC to build a subscription telehealth businessWhat makes for a great subscription in healthcareOpportunity size around content and telehealth SaaSHow they built a content machine onlineUser experience decisions that drove engagement and qualityRegulatory challenges when innovating in healthcareHow Sean has remained engaged building HealthTap for over a decadeImpact of pandemic— what was over-hyped and what acceleratedClosing questions Most talented person Sean has worked with and whyWhats something you believe that would surprise most peopleWho Sean’s heroes are and what inspires himWhat superpowers do you lean on day to dayLinksFollow Sean on TwitterRead more about HealthTapHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute.
EP18: Building customer obsessed products and culture, with Mari Baker, Silicon Valley veteran who was one of the first 30 employees and SVP at Intuit
Mar 22 2022
EP18: Building customer obsessed products and culture, with Mari Baker, Silicon Valley veteran who was one of the first 30 employees and SVP at Intuit
Mari has held a variety of incredible roles in Silicon Valley as a product veteran, company builder, and now board member. Mari started her career in startups. She was one of the first 30 people at Intuit and helped grow the company grow over 10 years into a public company with thousands of employees.At Intuit, Mari went from being a Product Manager for Quicken to SVP and got to work closely with industry legends like Scott Cook and Bill Campbell to shape Intuit’s products and culture. Intuit of course is well known for having one of the most customer centric product cultures and has successfully navigated multiple technology and platform shifts— from Command Line to GUI, PC to Web, and Web to Mobile. Mari shares some incredible lessons and insights from the early days that shaped Intuits product culture.We also talk to Mari about her more recent work serving on the boards of Stanford, and Blue Shield of California. We talk about how University boards work, Mari’s role in founding the Stanford Women’s Leadership Innovation Lab to tackle the under-representation of women in our industry, and opportunities for innovation in the healthcare space.This is an incredibly wide-ranging conversation where we cover so many interest topics spanning Mari’s incredible career as a product builder, company builder and board member.In this episode we discuss:Starting out in Silicon Valley and being early at Intuit What was the valley like at the start of the PC revolution?Intuit’s first product was Quicken (for personal finance), what was the original insight?What made you join Intuit when it was a small startup?How big was Intuit when you got there and when you left?How Intuit has built customer obsessed products across multiple decades Intuit was known to be extremely customer focus, how did y’all approach that in the early days and build the product culture? How did Quicken (personal finance) lead to Quickbooks (SMB accounting)?How did Mari approach marketing at a time when people were new to computers and software? Working with Scott Cook and Bill Campbell to shape Intuit products and culture How did Scott Cook approach product management during early days of software? How did Intuit build its customer centric culture? You got to work closely with Bill Campbell. What were his superpowers that helped him become such a legendary leader? Serving on the Board of Trustees at Stanford and setting up the Stanford Women’s Leadership Innovation Lab What does the Board of Trustees role at Stanford entail? What led you to setting up the Stanford Women’s Leadership Innovation Lab? Serving on the board of Blue Shield of California which is a non-profit insurer with 4.5m members and $21b in revenue Where do you see the biggest opportunities for technology to transform healthcare especially in a post Covid world? What’s your advice for healthcare founders trying to figure out trade-offs between B2B vs B2C business models?Closing questions Who is the most talented person Mari has ever worked with and whyWhat’s something you believe that would surprise most peopleWho are some of Mari’s heroes that she admiresWhat superpowers does Mari lean on day to dayLinksFollow Mari on LinkedinStanford Women’s Leadership Innovation LabHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summaries
EP17: Building remote controlled mobile vending machines, with Dmitry Shevelenko, who was early FB, Linkedin and Uber, before founding Tortoise
Mar 15 2022
EP17: Building remote controlled mobile vending machines, with Dmitry Shevelenko, who was early FB, Linkedin and Uber, before founding Tortoise
Dmitry is the founder of Tortoise ($11m raised), which is building remote-controlled mobile vending machines, which are the world’s first “smart stores”. It takes less than 15 seconds to complete a transaction with frictionless tap-to-pay user experience and Tortoise is piloting these robots in at least a dozen cities around the world. In this episode we talk about how Dmitry approached building a robotics and automation startup, and the many decisions that led Tortoise to where it is today.We also talk about Dmitry’s stellar early career and lessons learnt from being part of the early team at Facebook, Pulse, Linkedin and Uber. Dmitry shares his best career advice, some incredible stories from the early days of Facebook/Linkedin, and his experience at Uber where he championed the JUMP acquisition and overall multi-model mobility strategy.In today’s episode we discuss:Early Facebook experience What Facebook got right in the early days, and lessons from that experienceHow Dmitry managing the Zynga partnership from early days to it becoming the biggest single largest source of revenue for FB in 2009/10Some of the people Dmitry learnt the most during that experienceAdvice on how to navigate hyper growth, and Dmitry’s best career advicePulse, LinkedIn, and Uber experience How the culture at Linkedin differed from FBHow Dmitry ended up at Pulse working on early mobile/tablet experiencesHow the environment at Uber changed from before/after the media stormHow Dmitry framed the strategy that led to the JUMP acquisitionHow Uber thought about the business case for new modalitiesDmitry’s view on the big opportunity for micro-mobility (Bird, Lime, JUMP, etc.)Founding Tortoise and building autonomous delivery robots Core pillars to bring robotics / automation products to marketLast mile, middle mile and mobile vending use casesHow the Tortoise mobile smart store works (world’s first!)How Dmitry thinks about cost strategy for autonomous robotsHow Tortoise built a 15-second frictionless tap-to-pay checkout experienceHow much the mobile stores sell every hour and how many are live (dozen cities so far)What it takes to build and manufacture a robot (hardware iteration loops)Dmitry’s fundraising advice for a hardware and robotics startupClosing questions Most talented person Dmitry has ever worked withWhat superpowers does Dmitry lean on day to dayWho are some people that have given him a breakWho are some of Dmitry’s heroes that inspire himLinksFollow Dmitry on TwitterRead more about TortoiseTortoise mobile smart storesHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute.
EP16: Opportunities in Marketplaces, Future of Work, and Fintech, with Don Stalter, investor at Global Founders Capital and former Head of International at Airbnb & Groupon
Mar 2 2022
EP16: Opportunities in Marketplaces, Future of Work, and Fintech, with Don Stalter, investor at Global Founders Capital and former Head of International at Airbnb & Groupon
Don Stalter is a Partner at Global Founders Capital (GFC) and has an incredible portfolio of investments including Brex, Deel, CultureAmp, Checkr, FamPay and many more. Before transitioning into an investment role, Don was a co-founder of CityDeal which he sold to Groupon, and subsequently led International at both Groupon and Airbnb.In this conversation we talk about Don’s learnings from working on two of the most explosive marketplace companies of the last decade (Groupon and Airbnb), and trends/opportunities he’s seeing in Marketplaces, Future of Work, and Fintech.In today’s episode we discuss:Early career What led you into investment banking and M&A work early in your career?Having worked on blockbuster deals like Google/YouTube, Google/DoubleClick, Disney/Pixar, what were your biggest learnings from those experiences?Founding CityDeal and selling to Groupon What led you to founding CityDeal and ultimately sell to Groupon?What was your approach to running international at Groupon?What did Groupon get right in the early days, and what could they have done better?International at Airbnb What was your approach to international growth at Airbnb?How did you prioritize what to focus on during hypergrowth?Marketplace investments How do you evaluate marketplace businesses as an investor?What are your thoughts on B2B marketplaces which seem to be a new trend?What have been some of your learnings investing in digitization of older industries?Future of work investments What was your original thesis that led to investments like Deel, CultureAmp and Checkr?In a pod covid world, how do you think about remote tooling opportunity for productivity?Fintech investments What are some trends and thesis you’re most excited about?What are your observations on crypto and NFTs?Transition to VC What do you think makes a great operator vs a great VC?Has your operating background helped you as a VC?Closing thoughts What are your superpowers that you like to lean on day to day?Who are some people that have given you a meaningful break?What books have had an outsized impact on your life?LinksFollow Don on TwitterSome companies mentioned in the episode: Blueland, Cedar.ai, Checkr, Deel, Brex, KaratHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute.
EP15: Building crypto native products, with Qiao Wang, co-founder of Alliance DAO, the leading Web3 accelerator and builder community
Feb 22 2022
EP15: Building crypto native products, with Qiao Wang, co-founder of Alliance DAO, the leading Web3 accelerator and builder community
Qiao Wang is the co-founder of Alliance DAO, which is the leading web3 accelerator and builder community. In terms of impact, Alliance has helped accelerate 10% of the top crypto projects by market cap. Their most cohort had 30 companies building web3 products across DeFi, Social, NFTs and Gaming. Before Alliance, Qiao was the Head of Product at Messari which is a market intelligence product that provides advanced analytics for crypto.Special thanks to Roberto Riccio and Brian Ma for providing questions for this conversation.In today’s episode we discussCrypto Landscape What led to a perfect storm for decentralized technologies?How has pace of innovation progressed vs expectations?What could web3 native social networks/products look like?Opportunity Areas across DeFi, SocialNets, Gaming What are opportunity areas where Qiao is seeing startups get traction?What are some examples of interesting projects in different verticals?What are the main motivations for people playing games like Axie?What are some opportunities for financial products to build social experiences?Getting Messari off the ground to provide advanced analytics for crypto What was the unique insight when founding/building Messari?What were the first products / features that got PMF?How much to rely on intuition vs user feedback/research for crypto products?How did they approach pricing for their paid plans?How did they approach governance and tokens?Accelerating web3 with Alliance accelerator and community What is Alliance today and how did it start?How big is each cohort and what categories are most projects/companies in?How does the accelerator work and how does Alliance accelerate teams?What makes for a great Alliance founder?How to build Crypto Native products and companies When and how to launch a token?What are regulatory implications?How to fundraise for web3? How to vest?How to manage trade-offs between PMF and Tokens?How do SAFEs and SAFTs work?When and how to decentralize without losing vision and execution leadership?How to leverage DAOs in an effective way?Future of DAOs as Digital Nations How might DAOs re-shape society?What is the core value proposition of a DAO?How to build the right incentives with tokens and DAOs?How might DAOs enable digital nations with property rights and laws?Crypto and web3 trajectory What has to go right for crypto products to continue to go mainstream?Has crypto and web3 reached escape velocity? What are the biggest risks?Closing thoughts What are your superpowers that you like to lean on day to day?Who are some people that have given you a meaningful break?What books (or articles or podcasts) have had an outsized impact on your life?LinksApply to the next cohort of AllianceDAOFollow Qiao and AllianceDAO on TwitterHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute.
EP14: Bringing crypto loans to the real world, with Blake West, co-founder/CTO of Goldfinch, $500M DAO and $25M from a16z
Feb 3 2022
EP14: Bringing crypto loans to the real world, with Blake West, co-founder/CTO of Goldfinch, $500M DAO and $25M from a16z
In this wide-ranging conversation, we chat with Blake about his experiences starting out his professional career as a musician, and all the key experiences and trends that led him to founding the Goldfinch decentralized lending protocol (recent $25m Series A from a16z, and $500M DAO).This is an incredibly rich conversation where we explore so many interesting topics. Some select highlights: the similarities between being a musician and an engineer, and between being in a band and a startup. How the Goldfinch protocol works and Blake’s most ambitious vision for it. Advantages of setting up Goldfinch as a DAO. Predictions on NFTs. The areas where crypto really shines and the trends that are moving more and more economic activity on chain.Blake is a brilliant and clear thinker, and we learned so much from this conversation. We hope you enjoy it as much as we did.Episode HighlightsBeing a full-time musician after collegePutting small things together to make big things as a musician, and engineerJoy of working on a small group, and being in a band vs startupLearning to code after college and transitioning over to software engineeringEarly inflection points at Hint Health (Employee #1) and CoinbaseApproach to hiring engineers at GoldfinchHow Blake got into crypto and what got him interestedMagic of decentralization and many interfaces sitting on top of the same dataRecent LooksRare token launchWhat Goldfinch does and how it’s different from other crypto lending protocolsUnder-collateralized lending for real-world scenarios in a decentralized wayApproach to finding the right market and getting early PMF tractionHow the lending protocol works — across borrowers, backers and LPsMore liquidity as one of the places where crypto really shinesMost ambitious vision for the protocolTrends moving more economic activity on chainGoldfinch is setup as a DAO — how that worksTradeoffs between DAOs and Centralized OrganizationsThoughts on the current bear market cycleBlake’s secret to making rapid progress with GoldfinchWhat mission-driven means to BlakeDeFi advantages: natively global and interoperable by defaultPrediction on profile NFT pics coming trueCrypto wallets as bottomless digital backpacksPredictions on NFTs— “can’t lose” way for brands and creators to engage super fansBuilding great co-founder relationships and handling high pressure situationsRecruiting his initial boss at Coinbase to GoldfinchSuperpowers and book recommendationsStructure of Scientific Revolutions— the book that coined the term “Paradigm Shift”!LinksGoldfinch: the protocol bringing crypto loans to the real worldHummingbird Notation (early side project)Blake’s Op-Ed on NFTs from April 2021Follow Blake on TwitterHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute.
EP13: Building Communities and All Things DAO, with Don Ho, co-founder of OrangeDAO which is a collective of 1k+ YC founders helping build and accelerate web3
Jan 27 2022
EP13: Building Communities and All Things DAO, with Don Ho, co-founder of OrangeDAO which is a collective of 1k+ YC founders helping build and accelerate web3
In this conversation we chat about Don’s experiences in the crypto world as Managing Partner of QuantStamp, and through multiple cycles over the last decade. We spend most of our time talking about his recent experience co-founding OrangeDAO which is a collective of 1k+ YC founders helping build an accelerate web3.Don walks us through how he thinks about building communities, why DAO’s are exciting, and shares a breakdown of how the OrangeDAO was setup— across the early community, token design, building products, raising a venture fund, and how everything fits together.This is an inside look into how cutting edge DAO communities work today and why they’re such an exciting glimpse into the future. We hope you enjoy this conversation!Episode HighlightsGrowing up in Silicon Valley around people doing seemingly wacky, wild, strange thingsInvesting in Vietnam and facing remittance issues that led him to BitcoinCrypto as Financial Rails 3.0 and a wrapper to solve coordination problemsQuantStamp as a Verisign of crypto with over $40b of value securedMost surprising things since being early to crypto— rate of consumer adoptionDecentralize everything vs just things where crypto drives user valueHow B2B opportunities in crypto have evolved since 2017How to build a great community, and how to build a DAOWhy people organize- to express themselves and feel a sense of belongingKeys to enduring communities- clear purpose on what they’re trying to achieve, and why people should be joiningWhat is a DAO- communities that have a software layer and ownership component, with embedded incentive based coordination layerDAOs as a more scalable version of Co-Ops, on a blockchainHow to start a DAO, and how and why OrangeDAO was foundedOrangeDAO: largest collective of builders wanting to build or invest in Web3.. going from a WhatsApp group to a DAO to keep up with interest; today a collective of 1k+ YC foundersRaising an Orange Fund with $10m+ to invest in early Web3 companiesHow to setup a fund, and setup a DAO as the coordination layerHow ownership and governance works in a DAODesigning token economics for OrangeDAO and how everything fits togetherHow DAOs incorporate, get bank accounts and hold assetsProducts developed by OrangeDAO: YC gem for web2 to web3 oAuth and token gated communities, and LFG reputation game to bet on founders and companies on chainDon’s super powers and vision for OrangeDAOLinksOrangeDAO: collective of 1k+ YC founders helping build and accelerate web3QuantStamp: leaders in blockchains security and solutionsGreat tools for DAOs: Syndicate, Multis, Bank MercuryFollow Don on TwitterHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute.
EP12: Linda Zhang, early product leader at Faire ($12b co), on key growth unlocks in early days, ideal culture at fast growing companies, and founding Product Lessons
Jan 19 2022
EP12: Linda Zhang, early product leader at Faire ($12b co), on key growth unlocks in early days, ideal culture at fast growing companies, and founding Product Lessons
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 HighlightsEarly career at Bain and transitioning to startupsConsulting as a professional bootcampOperational and product culture at SnapTransitioning into PM roles at a startupFaire: b2b marketplace for brands/makers and retail storesWhat drew her to Faire ($12b co now) and early cultureKey growth unlocks at Faire, and building b2b viralityGoing from as Employee 14 ($50m valuation), to 300 employees ($2.5b valuation), and 1000 employees ($12b valuation)Transitioning to being a being a solo entrepreneurIdeal culture at fast growing companiesImportance of talent densityWriting/creating, building product toolkit, and starting product lessonsPower of building email listsTop Startups project to help people find great startups and jobsBuilding an audience: find a format that works for youHaving a “red pill”: what are you willing to say or share that no one else is saying or sharing?Mastering your own psychologySuperpowers, lucky break and booksLinksProduct ToolkitProduct LessonsTop StartupsFollow Linda on TwitterHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute.
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
EP11: Sander Daniels, co-founder of Thumbtack, on idea exploration, key phases in building a marketplace, and his secret to effective cofounder relationships
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 HighlightsGrowing up in DC and going to Law SchoolTwo big levers to make a difference— Politics and TechnologyThumbtack founding— weekly phone calls brainstorming ideas for a yearThumbtack today 13 years later— 900+ employees, over $500m raised, $3.2b valuationHow to come up with good ideas, and innovation as a deliberate processAlternate ideas and names explored (like “TimeStrapped!”)Marketplace liquidity as most important thing in early daysEarly days: solved supply first, then focussed on demand for 18mosKey moment in unlocking demand: early SEO insight and strategyKey to growing fast: one big channel where you go super deepBarriers to entry for more founders that prevent taking riskHow Sander overcame those barriers and how it shaped his thinking on riskChallenges raising early VC based on user growth alone— 45 A-round passesFour key phases: building supply, building demand, finding the right revenue model, hyper scalingChallenges and frustrations during the hyper scaling phaseReflection on power of focus, and also narrative/PRPower of hiring exec coaches to scale as founders and a teamBuilding strong co-founder relationships: structured approach, and long term focusAdvice for founders and building successful long term working relationshipsPutting on blinders and focussing on what you can controlScaling as a founder and building out multiple different areasOperating in your zone of genius to stay energized for 13+ yearsThumbtack’s culture and how they built and shaped itFramework for giving/recieving feedback and turning it into an action plan for growthReflections on Thumbtacks superpowers and shadows of those strengthsBook recommendation: Design Your LifeNew projects: (1) Scaled- bringing innovation to recruiting (2) New mobile dog grooming business that can train and up level anyone to earn $100k+Sander’s super power, lucky breaks, and book recommendationsLinksStart using Thumbtack to find local professionals for pretty much anythingHire People, Finance, Legal talent with ScaledFollow Sander @sanderdanielsHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute.
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 5 2022
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
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 HighlightsStarting her career on Wall St during the 2008 financial crisisCulture working in finance vs techFounding VIVE — what drove her to marketplacesVision to build a marketplace that helps salons acquire customersExplosive early demand — 14,000 customer waitlistChallenging unit economics — trade-offs between unlimited usage and credit systemExplorations — marketplace vs SaaS vs bundling CPG productsKey learning — PMF is about finding and meeting demand in a scalable way, unit economics and margins important even at early stagesJoining AfterPay to lead growth marketing for engagement and retentionApproach towards consumer vs merchant, and checkout product vs standalone appThoughts on fintech and potential risks in the systemHow startups build/validate a new lending product as a startup and risks to manageThoughts on DeFi and NFTs — both quickly going more and more mainstreamHow NFTs and e-commerce could merge and enable new products and marketing leversThoughts on what might happen if interest rates go up — mental model on opportunities if markets retreat or become more volatileSuper powers on spotting talent and hiring, people who have her a break, and booksLinksFollow Alanna @alannaeve on TwitterHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute.
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 16 2021
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
SummaryIn 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 HighlightsWorking on Chase Sapphire card at Visa and getting rejected for itChallenge of credit: needing credit to get creditHow credit score gets calculated and factors contributing to biasWhy women get rejected for a credit card more often than menSpeed of launching a card at a bank vs. as a startupConsiderations in designing a new cardBuilding Sequin as a debit card that builds creditHow to think about benefits as a fintech startup vs at scaleSurprising insights: huge appetite for knowledge, community and card designApproach to education and community building as a fintechVision for Sequin: full suite of credit products for women across every life stageGoing from fintech idea to prototype/MVP as a non-technical founderInsight: importance of credit utilization to build creditMoving fast without breaking anything as a fintechEarly next year: re-launching the debit card that builds launch with rewards partnersOpportunity to create hyper personalized products that grow with customersSuperpowers: capacity for empathy and how she's built it, and ability to pattern matchPeople who gave Vrinda a break, and book recommendationsLinksRead more about Sequin ($5.7m Seed) and get the card: Vrinda @vrinda_tweetHit subscribe to keep up with new episodes!Follow Ashish and Zane on Twitter for summariesClick here to give feedback — it only takes a minute.