Paradigm Shift

EP42: Evaluating and accelerating talent with Ali Partovi, Founder/CEO of Neo; and investor in Facebook, Airbnb, Uber, and more

In this episode we talk with Ali Partovi about lessons learned identifying, evaluating and accelerating talent across a long and storied career in Silicon Valley. We talk about his founder experience, great investments he's made, and his new accelerator Neo (which is something like YC 2.0). You can learn more about Neo here , and follow Ali to on Twitter to connect with him.

EP41: Bootstrapping Boast.ai to $10M ARR with No Marketing Team with Lloyed Lobo

EP40: AI as the next platform shift and investing in emerging technologies, with Elad Gil entrepreneur and investor

EP39: Lessons learned bootstrapping SwagUp to $100M+ in revenue with founder and CEO Michael Martocci

Michael Martocci is the Founder and CEO of SwagUp, a platform that makes it easy to create, automate and distribute swag globally. In this episode we talk about: Lessons learned bootstrapping SwagUp to over $100M in revenue Advice on managing cash flow and how Michael approached forecasting Michael's vision and SwagUp's unique position to reimagine the entire end to end workflow from the customer experience to the complex supply chain. This was a really fun conversation. We hope you enjoy it as ...

EP38: Michael Stoppelman, former SVP Engineering at Yelp and investor in 300+ companies, on building world class engineering teams and lessons learned scaling Yelp from 6 to 600 engineers

Michael Stoppelman is the former SVP of Engineering at Yelp and profilic angel investor in 300+ startups. In early 2007, he left Google to join Yelp, and helped scale Yelp Engineering from 6 to 600 engineers. In this conversation we talked about Michael's lessons learnt building and scaling a world class engineering team- from hiring to motivating to leading world class teams. We also talk about lessons learned from early days at Google, and his approach to angel investing where he has an extrem...

EP37: Building and funding enduring fintech companies, with Cameron Peake, Partner at Restive (fintech VC) and founder of early SMB neobank Azlo (almost $1B deposits)

Cameron Peake is a Partner at Restive Ventures, an early stage fintech focused VC fund. Previously Cameron was co-founder and CEO of Azlo, a company that provided online banking services for small businesses, entrepreneurs, and freelancers, and quickly grew to almost $1B in deposits. Cameron understands fintech from multiple vantage points: building for international markets, building one of the first neobanks in the US, and now funding early stage companies. In this conversation we discuss what...

EP36: Semil Shah (founder Haystack, early investor in DoorDash, Instacart, Figma) on the current fundraising market and building intuition to pick winners early

Semil is the founder and GP at Haystack, an early-stage VC firm with $450M+ AUM. He’s an investor in 200+ companies including DoorDash, Instacart, Hashicorp, Figma and more. In this conversation we discuss the current funding environment, Semil's approach to venture capital and making early investments, and his advice for founders starting a company and fundraising in today's market. This was a really fun discussion and we hope you enjoy it as much as we did! Links Follow Semil on Twitter Hit su...

EP35: Beerud Sheth, founder of Upwork ($1.5B public co) and Gupshup ($1.4B unicorn), on the resilience and grit needed to build two generational companies

Beerud Sheth in a rare founder who’s started not one, but two unicorns — UpWork and Gupshup. He’s seen a lot of pivotal moments in SV history — having started Upwork in 1998 before the dot com bubble, and Gupshup in 2005, three years before the GFC. Today, Upwork is a publicly traded company valued at $1.5B and Gupshup is a unicorn, last valued at $1.4B+ as of April 2021. In this conversation, we talk with Beerud about his experiences building UpWork and Gupshup across almost 25 years. Links Lea...

EP34: Finding product-market fit and blitzscaling a healthcare marketplace 25x in 18 months, with Wei Deng, CEO/Founder Clipboard Health ($1.3B)

Wei is the founder of Clipboard Health. Clipboard Health makes it really easy for nurses to search for jobs based on what they're qualified for and what they care about, and apply with one click. Over the last few years, Clipboard has have experienced rapid growth and become the leading marketplace for healthcare profesional to find on-demand shifts at healthcare institutions. Clipboard has raised $94M from top VCs that include YC, Initialized, Caffeinated Capaital, and Sequoia, most recently at...

EP33: Building and scaling network-based enterprise businesses with James McGillicuddy, former Head of Strategy at Carta ($7.4B) and COO SourceGraph ($2.6B)

In this conversation, we speak with James McGillicuddy. James was previously Head of Strategy at Carta ($7.4B valuation) where he brought products like CartaX to market, and before that was the COO and early team member of SourceGraph — a universal code search tool company valued at $2.6B. He was also early at RelateIQ (acquired by Salesforce for $390M) and played college football for Stanford under Jim Harbaugh. Some highlights: how James approached decisions on which early stage companies and ...

EP32: Building and launching cross-chain crypto infrastructure, with Bryan Pellegrino, founder/CEO of Layer Zero ($140M Series A)

Bryan is the founder of LayerZero Labs, which is an omnichain interoperability protocol that unites decentralized applications across disparate blockchains, enabling cross-chain applications. LayerZero Labs is building foundational crypto infrastructure. Since being founded in 2021, the company has raised over $140M from top investors including Sequoia Capital, a16z, Tiger Global, Coinbase, Cristies, Paypal, Polygon and Dapper Labs. In this conversation, we discuss the LayerZero founding story, ...

EP31: Kunal Shah on building breakout consumer internet products, founding Cred ($6.4B) and Freecharge ($450M exit), and angel investing in 200+ Indian startups

Kunal Shah is a serial entrepreneur and founder of two iconic Indian companies -- CRED and Freecharge. CRED is an Indian consumer fintech that is valued at over $6.4B, and Freecharge was one of the earliest Indian fintechs that sold to Snapdeal in 2015 for $450M. Kunal has an unmatched track record not just as a founder, but also as an investor and thinker. He’s a prolific angel investor in over 200+ Indian startups and shares insightful, bite-sized philosophical wisdom on Twitter with over 700K...

EP30: Building web3 email, drive and docs with a privacy-first and decentralized approach, with Andrew Milich, founder of Skiff ($10M Series A led by Sequoia)

Andrew is the founder of Skiff, which is a privacy-first, end-to-end encrypted, wallet native workspace with email, file sharing, and collaboration. Skiff has hundreds of thousands of users and is part of a broader trend towards privacy-first and decentralization. Skiff is backed by Sequoia Capital who led their seed and Series A. In this conversation we discuss Andrew’s path to building privacy-first products, approach to finding Product-Market Fit with Skiff, and the various tarde-offs and opp...

EP29: Keith Rabois on navigating the downturn, developing good judgement, and building an iconic company

Keith is a Silicon Valley legend— an accomplished operator, founder, and investor. He started his career as an early executive at PayPal, LinkedIn and Square, before going on to co-found companies like OpenDoor (which IPO’d in 2020) and OpenStore. He’s currently a General Partner at Founders Fund and Co-Founder/CEO of OpenStore. Along the way, he’s made incredible investments as an angel and VC in companies like DoorDash, Affirm, Stripe, YouTube, Palantir, Airbnb, Ramp, Faire, and many more. In ...

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 lesso...

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. A...

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 j...

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...

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 Partne...

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 pu...

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 z...

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 l...

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 e...

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 insurance How it works from user experience to business model Types of conditions and issues that can be treated through primary care How HealthTap approaches different use cases and care scenarios Building a healthcare product and company How to get ...

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 o...

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 ...

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 tre...

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 ...

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...

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 growin...