Paradigm Shift

Latest Episodes:

EP32: Building and launching cross-chain crypto infrastructure, with Bryan Pellegrino, founder/CEO of Layer Zero ($140M Series A) Dec 06, 2022

Show notes

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, how Bryan approached building complex decentralized infrastructure, their explosive launch and seemingly immediate product-market fit, and the cross-chain opportunity space.
This was an incredibly fun conversation and we learnt a ton from Bryan about the "behind the scenes" of building and launching widely used crypto infrastructure.
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EP31: Kunal Shah on building breakout consumer internet products, founding Cred ($6.4B) and Freecharge ($450M exit), and angel investing in 200+ Indian startups Nov 29, 2022

Show notes

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 followers.
In this conversation we explore frameworks and insights that have guided Kunal's approach to building consumer internet products, the "delta-4" framework he uses to evaluate the potential for a breakout product, how consumer behavior changes in trust vs trust-less societies, and his approach to angel investing.
In the closeout, we ask Kunal about the most difficult/challenging feedback he has received and how he processed it, and superpowers he has identified in himself that he leans on day to day.
Links

Follow Kunal and CRED on Twitter

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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) Oct 30, 2022

Show notes

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 opportunities when building privacy-forward and web3/decentralized products.

This was a really fun conversation and we learnt so much about what why privacy products matter, their path to increasing mainstream adoption, the business models that are working, and how companies like Skiff are taking us into an exciting future where technology continues to democratize and protect privacy and digital freedom.

Topics discussed:

How did you end up working on privacy-first products?
What is your vision for Skiff and what does the product to today?
How did you approach integrating crypto login with meta-mask and decentralization?
How did you approach being privacy-first from the ground up? How does that affect the user experience and user journey?
How did you approach the trade-offs between building on centralized and decentralized APIs/components for the best user experience? Eg: onboarding, account recovery, etc.
How did you approach e2e encryption and interoperability when building a privacy-first Skiff email product?
How did you get started building the initial Skiff MVP and who was your first user?
What are your thoughts on competing with very mature incumbent products like GMail, Drive, Notion and Evernote? How have you approached it?
How did you build conviction in the opportunity around Skiff and the market opportunity?
What have you noticed are some triggers that make people switch to a privacy-first email or collaboration product like Skiff? What are some archetypes of people who seek out these products and switch?
Since you don’t track your users, how do you figure out who they are, what they want and figure out how to improve the product?
How do you think about the global opportunity and internationalization?
How do you cross the user adoption chasm to mainstream adoption from where we are today to privacy-first networked products like email?
How do you think about business models for Skiff and privacy products?
What made you decide to be consumer first vs enterprise and b2b focused?
Who should use Skiff and how should they use it?
Zooming out what are some areas in the privacy space that you’re most excited about?
Closeout questions: what is the most challenging or difficult feedback you’ve received and how have you processed it? What are some superpowers you’ve identified in yourself that you like to lean on?

Links

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Signup for Skiff for end to end encrypted web3 email, drive and docs

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EP29: Keith Rabois on navigating the downturn, developing good judgement, and building an iconic company Sep 08, 2022

Show notes

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 this conversation we ask questions that span three broad areas: how to grow through a downturn, how to develop good judgement, and how to build an iconic company.

This episode is packed with incredible insights and actionable advice from Keith. We hope you enjoy this conversation, and learn as much from it as we did.
In this episode we discuss:

Growing through a downturn
- Given the current market correction underway, what do you think happens next?
- What advice do you have for founders starting companies in this market context?
- You’ve said you believe the best companies are built in the public markets. What do you think needs to happen for more companies to go public within 4-6 years vs 10-15 years?
- What do you think is the right time (or maturity level) for a company to go public?
Developing good judgement
- You have been extremely successfully at investing super early. What has been your approach to making investments when it’s just a team and a keynote deck?
- You’ve talked about how you look for a “spark” when making early-stage investments. Could you describe a time you’ve seen that? What has it looked like?
- Could you share some examples where things have not gone well and how you’ve approached those situations?
- How have you honed your skill in evaluating people and opportunities, and what advice do you have for someone trying to improve their own judgement?
- How much overlap do you think there is between the skills used to hire and the skills used to evaluate a founder? How do you approach assessing people in both those contexts?
Building an iconic company
- You’ve seen a lot of companies navigate the path to product-market fit. What approaches you’ve seen work particularly well? What has been your own approach to getting to PMF?
- Post PMF, how do you think about the trade-off between growth and efficiency? Do you think the current market context changes the traditional blitz-scaling strategy?
- When evaluating investment opportunities, to what extent are you thematically driven vs opportunistically driven?
- You’ve talked about how people often don’t map their time to their priorities well. As a VC and an operator, how do you approach setting priorities and what does that look like on a week-to-week basis?
- How have you approached coaching/helping founders and new managers/executives better prioritize their time towards the highest leverage activities?
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?
- Anything you’re reading right now that you’d recommend?

Links

Follow Keith, Founders Fund and OpenStore on Twitter

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EP28: Building an open source powered product and company, with AppSmith Co-Founder/CEO Abhishek Nayak Jul 20, 2022

Show notes

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?

Links

Learn more about AppSmith
Follow Abhishek and AppSmith on Twitter

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EP27: Building crypto products for mainstream users, with CoinList Co-Founder and Eco Co-Founder/CEO Andy Bromberg Jul 11, 2022

Show notes

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?

Links

Learn more about Eco
Follow Andy and Eco on Twitter

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EP26: Reimagining healthcare from first principles, with Forward Founder/CEO Adrian Aoun Jun 19, 2022

Show notes

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?

Links

Learn more about Forward
Follow Adrian and Forward on Twitter

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EP25: Founding and scaling a logistics unicorn, with ShipBob Co-Founder/CEO Dhruv Saxena Jun 10, 2022

Show notes

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?

Links

Learn more about ShipBob
Follow ShipBob on Twitter

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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 06, 2022

Show notes

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?

Links

Follow Nikhil on Twitter
Learn more about Insight Partners

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EP23: Building in public and the future of AI powered creative tools, with Paul Yacoubian, founder/CEO of Copy.AI May 22, 2022

Show notes

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
1. How did you get started building in public?
2. What principles guide your online content?
3. What have been the benefits of building online?
4. How has it helped you get early adopters and investors?
5. How do you approach how much time to spend on twitter?
6. What advice do you have for someone getting started building in public?
Copy.AI and future of AI powered tools
1. What is copy AI and what is the long term vision?
2. How do people use Copy AI to generate copy and ideas?
3. How do you make AI better at writing copy?
4. What are some really popular use cases?
5. How much of the AI is off-the-shelf vs your own models?
6. How unique and defensible is the AI in workflow tools?
7. How do users make the product better in workflow tools?
8. What channels have worked best to acquire your 1M registered users?
9. What has engagement, retention and monetization looked like?
10. What do you think the future of AI powered creative tools looks like?
Closeout questions
1. Who is the most talented person you have worked with and why?
2. What are some superpowers you have identified in yourself and like to lean on?

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