Paradigm Shift

Latest Episodes:

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

Show notes

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
1. How did you go from being a collegiate baseball player to working at Google?
2. What did you learn at Google based on how they approached recruiting?
3. How did Google approach Hiring Committee and what did you learn from it?
4. What did the recruiting funnel look like at Google vs startups later in your career?
5. What did speed of hiring look like at Google vs Facebook, startups, etc?
Leading recruiting for DoorDash during hyper growth from 50 to 800+
1. How did you end up at DoorDash and what was the scale like? h/t Kym Lee!
2. You’ve said Tony is the best recruiter in the world. What makes him so great?
3. What were you optimizing for when you moved to DoorDash and why did you pick them?
4. What were the challenges recruiting and how did you approach it?
5. How did you maintain and raise the hiring bar while scaling quickly?
6. How did you get hiring managers to own sourcing and recruiting outcomes?
7. What KPIs and funnel metrics were you focused on each month/quarter?
8. How did you hire people better than you? How did you help people grow?
Leading the HR function at Carta as CPO
1. What led you to Carta? What was the state of the company when you got there?
2. What was the nature of the network effect at Carta that fueled the business?
3. What are your observations on some of the problems with equity today?
4. What are some trends you’ve seen in the talent and equity market?
Founding story and vision for Continuum
1. What is Continuum and what problems are you solving?
2. What are you hearing from companies and execs on fractional opportunities?
3. What is your vision for Continuum?
4. What has been the most humbling part of being a first-time founder?
Recruiting and HR at startups
1. What is your HR advice for early-stage founders?
2. How should founders think about HR strategically?
3. When should a startup hire their first recruiter?
4. What do you look for when hiring recruiters?
5. How do you think about the value of an advisor?
6. What makes someone a great recruiter?
Closeout questions
1. What is the most difficult feedback you’ve received?
2. What are you optimizing for at this point in your career and how has that evolved?
3. What are some of your superpowers that you find yourself leaning on often?

Links

Follow Nolan on Twitter
Read Nolan’s thread on he helped DoorDash grow from 50 to 800+ employees
Check out Continuum— to hire an exec or join as an exec

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries
Click 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 02, 2022

Show notes

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
1. What led you to tech entrepreneurship?
2. What led you to found Sheroes?
3. What problems do you solve for women?
4. What are gender rankings and how do they work?
5. How are users using Sheroes today?
6. How does Sheroes unlock more opportunities for women?
7. How did you grow to a 15M community?
8. How do you build and maintain trust in the product?
9. How do you make money and what’s your current revenue?
Fintech and startup ecosystem in India
1. What led you to found Mahila Money— banking for women?
2. What is the current state of fintech in India?
3. Where do you see the biggest fintech opportunities in India?
Closeout questions
1. Who is the most talented person you have worked with and why?
2. What are some things you believe that would surprise most people?
3. What are some of your superpowers that you’ve learnt to lean on often?

Links

Follow Sairee on Twitter
Check out Sheroes and Mahila Money

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries
Click 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 18, 2022

Show notes

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
1. What was your first DeFi experience and aha moment?
2. What led you from skepticism to curiosity to excitement?
3. What DeFi is and how does it work?
4. How to understand risk, returns and yields?
How DeFi yield farming works and generates passive income
1. How does DeFi work in a decentralized way and eliminate middlemen?
2. How do transactions between two assets or parties happen in DeFi?
3. How does decentralized finance increase automation, lower costs, and increase access to yield/revenue from automated market making?
4. What is driving yields and rates of return on assets in DeFi?
How to identify, research and evaluate yield opportunities/risks
1. What are the different ways to invest and earn a return in DeFi?
2. How do you research opportunities and filter signal from noise?
3. How do you evaluate potential based on narrative/speculation, and cashflow/DCF?
4. What are some examples of crypto projects with low DCF valuation right now?
5. How do find information/data to analyze yield farming opportunities?
6. What are the categories of risks a crypto investor should bear in mind?
7. What is your framework for evaluating risk, returns and constructing portfolios?
8. What are typical returns for low risk, med risk and high-risk opportunities?
9. How to earn 32.9% ROI per year through a simple risk management portfolio framework?
10. How do you think about counter-party risk for stable coins?
Outlook on future of DeFi and yields
1. What are the biggest barriers to more trust and adoption of DeFi?
2. What is your take on government oversight and the regulatory landscape?
3. Whats your outlook on yield farming opportunities in the current crypto landscape?
Closing questions
1. Who is the most talented person you have ever worked with?
2. What is something you believe that would surprise most people?
3. What superpowers do you like to lean on day to day?
4. Who are some people that have helped you along the way?

Links

Follow Kedric on Twitter
Check 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 gap

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries
Click 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 05, 2022

Show notes

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
1. Affordable solution for all Americans regardless of whether they have insurance
2. How it works from user experience to business model
3. Types of conditions and issues that can be treated through primary care
4. How HealthTap approaches different use cases and care scenarios
Building a healthcare product and company
1. How to get early traction
2. Importance of patience and resilience
3. Maximizing luck surface area
4. Being early to telehealth and growing with the market
5. Impact of pandemic to tele-health
Exploring multiple business models in healthcare
1. Connecting consumers online with 90k physicians
2. Building a trusted Doctor powered UGC powerhouse
3. Leveraging UGC to build a subscription telehealth business
4. What makes for a great subscription in healthcare
5. Opportunity size around content and telehealth SaaS
6. How they built a content machine online
7. User experience decisions that drove engagement and quality
8. Regulatory challenges when innovating in healthcare
9. How Sean has remained engaged building HealthTap for over a decade
10. Impact of pandemic— what was over-hyped and what accelerated
Closing questions
1. Most talented person Sean has worked with and why
2. Whats something you believe that would surprise most people
3. Who Sean’s heroes are and what inspires him
4. What superpowers do you lean on day to day

Links

Follow Sean on Twitter
Read more about HealthTap

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries
Click 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

Show notes

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 why
- What’s something you believe that would surprise most people
- Who are some of Mari’s heroes that she admires
- What superpowers does Mari lean on day to day

Links

Follow Mari on Linkedin
Stanford Women’s Leadership Innovation Lab

Hit 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

Show notes

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
1. What Facebook got right in the early days, and lessons from that experience
2. How Dmitry managing the Zynga partnership from early days to it becoming the biggest single largest source of revenue for FB in 2009/10
3. Some of the people Dmitry learnt the most during that experience
4. Advice on how to navigate hyper growth, and Dmitry’s best career advice
Pulse, LinkedIn, and Uber experience
1. How the culture at Linkedin differed from FB
2. How Dmitry ended up at Pulse working on early mobile/tablet experiences
3. How the environment at Uber changed from before/after the media storm
4. How Dmitry framed the strategy that led to the JUMP acquisition
5. How Uber thought about the business case for new modalities
6. Dmitry’s view on the big opportunity for micro-mobility (Bird, Lime, JUMP, etc.)
Founding Tortoise and building autonomous delivery robots
1. Core pillars to bring robotics / automation products to market
2. Last mile, middle mile and mobile vending use cases
3. How the Tortoise mobile smart store works (world’s first!)
4. How Dmitry thinks about cost strategy for autonomous robots
5. How Tortoise built a 15-second frictionless tap-to-pay checkout experience
6. How much the mobile stores sell every hour and how many are live (dozen cities so far)
7. What it takes to build and manufacture a robot (hardware iteration loops)
8. Dmitry’s fundraising advice for a hardware and robotics startup
Closing questions
1. Most talented person Dmitry has ever worked with
2. What superpowers does Dmitry lean on day to day
3. Who are some people that have given him a break
4. Who are some of Dmitry’s heroes that inspire him

Links

Follow Dmitry on Twitter
Read more about Tortoise
Tortoise mobile smart stores

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries
Click 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 02, 2022

Show notes

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
1. What led you into investment banking and M&A work early in your career?
2. 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
1. What led you to founding CityDeal and ultimately sell to Groupon?
2. What was your approach to running international at Groupon?
3. What did Groupon get right in the early days, and what could they have done better?
International at Airbnb
1. What was your approach to international growth at Airbnb?
2. How did you prioritize what to focus on during hypergrowth?
Marketplace investments
1. How do you evaluate marketplace businesses as an investor?
2. What are your thoughts on B2B marketplaces which seem to be a new trend?
3. What have been some of your learnings investing in digitization of older industries?
Future of work investments
1. What was your original thesis that led to investments like Deel, CultureAmp and Checkr?
2. In a pod covid world, how do you think about remote tooling opportunity for productivity?
Fintech investments
1. What are some trends and thesis you’re most excited about?
2. What are your observations on crypto and NFTs?
Transition to VC
1. What do you think makes a great operator vs a great VC?
2. Has your operating background helped you as a VC?
Closing thoughts
1. What are your superpowers that you like to lean on day to day?
2. Who are some people that have given you a meaningful break?
3. What books have had an outsized impact on your life?

Links

Follow Don on Twitter
Some companies mentioned in the episode: Blueland, Cedar.ai, Checkr, Deel, Brex, Karat

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries

Click 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 21, 2022

Show notes

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 discuss

Crypto Landscape
1. What led to a perfect storm for decentralized technologies?
2. How has pace of innovation progressed vs expectations?
3. What could web3 native social networks/products look like?
Opportunity Areas across DeFi, SocialNets, Gaming
1. What are opportunity areas where Qiao is seeing startups get traction?
2. What are some examples of interesting projects in different verticals?
3. What are the main motivations for people playing games like Axie?
4. What are some opportunities for financial products to build social experiences?
Getting Messari off the ground to provide advanced analytics for crypto
1. What was the unique insight when founding/building Messari?
2. What were the first products / features that got PMF?
3. How much to rely on intuition vs user feedback/research for crypto products?
4. How did they approach pricing for their paid plans?
5. How did they approach governance and tokens?
Accelerating web3 with Alliance accelerator and community
1. What is Alliance today and how did it start?
2. How big is each cohort and what categories are most projects/companies in?
3. How does the accelerator work and how does Alliance accelerate teams?
4. What makes for a great Alliance founder?
How to build Crypto Native products and companies
1. When and how to launch a token?
2. What are regulatory implications?
3. How to fundraise for web3? How to vest?
4. How to manage trade-offs between PMF and Tokens?
5. How do SAFEs and SAFTs work?
6. When and how to decentralize without losing vision and execution leadership?
7. How to leverage DAOs in an effective way?
Future of DAOs as Digital Nations
1. How might DAOs re-shape society?
2. What is the core value proposition of a DAO?
3. How to build the right incentives with tokens and DAOs?
4. How might DAOs enable digital nations with property rights and laws?
Crypto and web3 trajectory
1. What has to go right for crypto products to continue to go mainstream?
2. Has crypto and web3 reached escape velocity? What are the biggest risks?
Closing thoughts
1. What are your superpowers that you like to lean on day to day?
2. Who are some people that have given you a meaningful break?
3. What books (or articles or podcasts) have had an outsized impact on your life?

Links

Apply to the next cohort of AllianceDAO
Follow Qiao and AllianceDAO on Twitter

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries

Click 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 02, 2022

Show notes

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 Highlights

Being a full-time musician after college
Putting small things together to make big things as a musician, and engineer
Joy of working on a small group, and being in a band vs startup
Learning to code after college and transitioning over to software engineering
Early inflection points at Hint Health (Employee #1) and Coinbase
Approach to hiring engineers at Goldfinch
How Blake got into crypto and what got him interested
Magic of decentralization and many interfaces sitting on top of the same data
Recent LooksRare token launch
What Goldfinch does and how it’s different from other crypto lending protocols
Under-collateralized lending for real-world scenarios in a decentralized way
Approach to finding the right market and getting early PMF traction
How the lending protocol works — across borrowers, backers and LPs
More liquidity as one of the places where crypto really shines
Most ambitious vision for the protocol
Trends moving more economic activity on chain
Goldfinch is setup as a DAO — how that works
Tradeoffs between DAOs and Centralized Organizations
Thoughts on the current bear market cycle
Blake’s secret to making rapid progress with Goldfinch
What mission-driven means to Blake
DeFi advantages: natively global and interoperable by default
Prediction on profile NFT pics coming true
Crypto wallets as bottomless digital backpacks
Predictions on NFTs— “can’t lose” way for brands and creators to engage super fans
Building great co-founder relationships and handling high pressure situations
Recruiting his initial boss at Coinbase to Goldfinch
Superpowers and book recommendations
Structure of Scientific Revolutions— the book that coined the term “Paradigm Shift”!

Links

Goldfinch: the protocol bringing crypto loans to the real world
Hummingbird Notation (early side project)
Blake’s Op-Ed on NFTs from April 2021
Follow Blake on Twitter

Hit subscribe to keep up with new episodes!

Follow Ashish and Zane on Twitter for summaries

Click 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

Show notes

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 Highlights

Early career at Bain and transitioning to startups
Consulting as a professional bootcamp
Operational and product culture at Snap
Transitioning into PM roles at a startup
Faire: b2b marketplace for brands/makers and retail stores
What drew her to Faire ($12b co now) and early culture
Key growth unlocks at Faire, and building b2b virality
Going from as Employee 14 ($50m valuation), to 300 employees ($2.5b valuation), and 1000 employees ($12b valuation)
Transitioning to being a being a solo entrepreneur
Ideal culture at fast growing companies
Importance of talent density
Writing/creating, building product toolkit, and starting product lessons
Power of building email lists
Top Startups project to help people find great startups and jobs
Building an audience: find a format that works for you
Having a “red pill”: what are you willing to say or share that no one else is saying or sharing?
Mastering your own psychology
Superpowers, lucky break and books

Our TOPPODCAST Picks

Follow Us

Stay Connected

Related Podcasts

Links

Stay Connected