Few Y in the Valley guests have been as insightful, candid, and vulnerable as Jeetu Patel, Cisco’s EVP and GM of Security and Collaboration. This episode spans the gamut — from how to build products with ‘intrinsic pull’ to the disruption of AI, improving remote collaboration, and on a more serious note — how Jeetu is building a relationship with grief and loss. Jeetu’s candor is refreshing, and as a leader at a company with more than 70,000 people globally, it’s clear how and why he’s earned such an influential role. This isn’t an episode you want to miss.

Show Notes

• 1:15: The Con-Man
• 7:39: Navigating the grief journey
• 15:51: ChatGPT’s secret power
• 21:48: Disruption + the need for AI regulation
• 32:09: What sets WebEx apart
• 42:53: Building strong, deep teams…remotely
• 45:50: The Sprint

Dan Bjerke knows a thing or two about driving growth. As the Head of Clover, he’s driven explosive revenue growth, expected to surpass $1.8 billion by the time 2022 winds down. He’s steered Clover’s business to become one of the most formidable players building POS platforms today, managing more payment volume than Square. Clover’s also helped more than 700K small and mid-sized businesses thrive, thanks in part to the POS solutions they offer. So when it comes to growth—Dan knows what it takes. It’s part of the reason Ashish sat down with him: over the course of their conversation, Dan shares what the three primary drivers of Clover’s growth are, his insights for aspiring leaders looking to scale a business the right way, and why it’s crucial to be obsessed about talent as any organization expands. So sit down, strap in and see how the Head of Clover gets it done. 

Show Notes

• 1:37: All in the family
• 5:11: Understanding Clover today
• 8:20: What powers Clover’s explosive growth
• 16:21: Attracting leading talent 
• 25:40: Helping businesses thrive
• 33:27: The importance of failure
• 37:40: The Sprint

It’s September. And like every previous year in recent memory, California is on fire. Again. Evolving problems, though, call for evolved solutions. Enter FIREWATCH— a first-of-its-kind NFT project designed to fund fire prevention in California. Buying one of the pop-art NFTs in this collection of California landscapes delivers 100% of proceeds to forest conservation efforts through the project’s official non-profit partner, One Tree Planted. YML created this NFT experience by building on Solana, an eco-friendly blockchain, ensuring every transaction is carbon-offset. Ashish focuses this episode on FIREWATCH, alongside a pair of guests — Anatoly Yakovenko, Co-Founder of Solana, as well as Matt Hill, Chief Environmental Evangelist at One Tree Planted. Together they unpack the FIREWATCH origin story, the promise of Web3, what the future holds for crypto, and how crucial it is blockchains dramatically decrease their environmental footprint. But they don’t stop there. Matt shares the secrets to One Tree Planted’s massive growth, what it takes to limit the severity of wildfires, and his best tips on building a nonprofit from the ground up.

Show Notes

• 2:25: Welcome to One Tree Planted and Solana
• 5:15: One Tree Planted’s explosive growth
• 6:52: Proof of stake and an energy-efficient blockchain 
• 9:10: The future of crypto 
• 18:20: The promise of Web3
• 19:44: Tackling wildfire today
• 24:28: Launching a nonprofit
• 26:22 The wrap-out

Adrian Aoun, Forward Heath’s CEO and Founder, is anything but one-dimensional. He wants Forward Health to change how the world does health care; to increase both access and improve quality all at once. On this episode of Y in the Valley, Ashish chats with Adrian about his 30-year plan to get Forward’s offering — focused affordable services centered on prevention and protecting long-term health — to not just millions of people in the US, but billions around the globe. They discuss the role bleeding-edge technology plays in Forward’s patient experience, and why thinking about healthcare as a product rather than a service can help the health industry level up to meet tomorrow’s challenges head on. (Note: episode includes explicit language.)

Show Notes: 

• 2:21: Immigration, assimilation + the insight that followed
• 7:00: Launching his first company 
• 12:45: Working as an advisor to the Obama Administration
• 16:27: Fast forward to…Forward Health
• 25:40: Why healthcare should be a product, not a service 
• 36:46: Landing Forward’s first 1k customers
• 46:08: The Sprint

Mental health is health. Perhaps that seems obvious today, but the fight for awareness and empathy within mental health is decades old, and ongoing. Headspace brings mindfulness and meditation to over 30M users globally and positions mental wellness as a true north for their brand. On this episode of Y in the Valley, Ashish interviews Leslie Witt, Headspace’s Chief Product and Design Officer, who shows how the right combination of technology and design can amplify the importance of mental health and  wellness. Leslie walks us through how Headspace’s mindfulness app evolved to connect users to clinical treatment, why habits often ebb and flow, and the powerful role experimentation plays in driving lasting, enduring product outcomes. 

Show Notes: 

• 1:41: Letters to the President 
• 9:02: Coming to Headspace during a Pandemic
• 13:25: Why Headspace Needed to Step Up
• 20:35: The Secret About Habit Formation
• 26:31: Establishing an Enduring Brand
• 30:32: Evolving into Headspace Health
• 34:39: Building in Teams in Today’s Environment
• 40:09: The Sprint

Talent is everywhere. It’s something Gabe Dalporto, CEO of Udacity, understands well. Udacity is an edtech platform working to provide societal-level change by leveling up the workforce through nanodegrees in specialized fields. For some, their fields are being threatened by tech advancements that could render their career obsolete. For others, folks are working in low-skill jobs with no way out. But Gabe has the solution. In this episode, Gabe unpacks how he went from studying nuclear engineering at MIT to leading a company that’s had more than fourteen million users to date. He takes us through the detours, the risks and the wins. But Udacity is just getting started—hit play to learn more.

Show Notes

2:30 - 7:40: Cultivating a passion for education through nuclear engineering

7:41 - 14:32: Revitalizing Lending Tree with explosive growth 

14:33 - 18:17: What motivated the switch to Udacity 

18:18: - 25:59: How Udacity is upskilling and transforming lives  

26:00 - 32:15: The challenges Udacity is rising to meet 

32:16 - 36:56: How Udacity is embracing diversity, equity and inclusion

37:57 - 44:13: Enduring the challenges the pandemic brought 

44:14 - 48:22: The Sprint

“Get used to the grind.” Despite saying those words with a smile, Sasha Siddhartha, Co-founder and CTO of Thrive Market, doesn't sugarcoat it. The path to building a company is arduous, and Sasha unpacks how he’s built his company, Thrive Market, the online grocer dedicated to organic and natural foods, from an idea with friends to a national grocery with 1M subscribers across the US. Sasha recalls the uncertainty his co-founding team felt at launch and the hypergrowth that followed, highlighted by a serious spike over the last 18 months as Covid forced countless people to online grocery shopping. Thrive is proving to be more than just a ‘digital Whole Foods’: it’s a challenger brand and the next generation of grocery in a remote, distributed world.

Show Notes:

• 1:40: Embarking on the startup journey 
• 6:48: How the initial idea behind Thrive evolved 
• 15:02: Unearthing the gap in the market
• 20:12: Keeping hypergrowth under control
• 23:58: Learning from those early experiments that failed
• 31:07: Designing Thrive for today’s consumer
• 36:15: Sasha’s advice to tomorrow’s founders 
• 37:25: The Sprint 

The future is electric — just ask Gregor Hembrough, President of Polestar USA, a Swedish, electric vehicle company rapidly growing across the US. Initially launched as a high-performance unit within Volvo, Polestar’s vehicles are as thoughtful as they are beautiful; not just the design of the surface details, but the sustainable technology that lives under the hood. Gregor explores Polestar’s origin story, detailing how a company dependent on gasoline pivoted to electric and identified a gap in the marketplace it was designed to fill. Along the way, he exposes the biggest challenges the EV business faces, and how Polestar is uniquely positioned to fuel the future with their commitment to sustainability, technology and design. So hop in, buckle your seatbelt and listen as Ashish and Gregor dish on all things EV.

Show Notes

• 4:45: Cultivating his love for cars, Gregor spent 20+ years at Volvo before joining Polestar 
• 9:29: Why the future is changing the EV adoption rate 
• 13:15: How battery anxiety is going to be a thing of the past 
• 17:01: Why someone would buy a Polestar over a Tesla 
• 23:40: How the car buying experience is doing a 180°
• 27:22: The key challenges facing the EV industry today
• 37:31: Why Polestar is evolving what a car salesman can be 
• 40:24: The Sprint

Figma has transformed the silo’d world of design into a collaborative, multiplayer game. Dylan Field, CEO and Co-Founder of Figma, shares his journey building the product and how he dropped out of college and ultimately scaled Figma to a $2B valuation. At YML, we use Figma across all disciplines for the end to end experience — not just design. It’s become a vital tool in building world-class digital products for both our team and our clients. Lastly, we're excited to welcome YML’s Chief Creative Officer, Stephen Clements, as a co-host for this episode.

Show Notes: 

1:59: The impact Figma has on YML

9:18: The early experiments before Figma was born

14:27: Building a multiplayer design tool when people insisted it wouldn’t work

19:26: Crafting a culture that stays the same through massive growth

25:11: How FigJam is inviting even more collaboration between teams

32:19: Why Figma waited years to start charging customers

33:20: Framework for building culture when the team is remote 

49:49: The Sprint

Assaf Wand knew how broken the home insurance market was: an industry more interested in covering antiquated items like gold bullion and mausoleums rather than the electronics and home office equipment you need to get through your day. So Wand went to work, unafraid of the insurance world’s red tape, rules and regulations, and launched Hippo. Designed to be a proactive, customer-centric experience, Hippo has made a swift impact with more than $400M premiums in force, now available in 34 states. After announcing its plans to go public, Hippo, an InsuraTech unicorn, is now valued at $5B. Discover how Wand navigates the complex world of insurance to build a home insurance alternative that serves real people’s real needs.

2:09: What the Israeli Air Force taught him about entrepreneurship

6:40: Seeing Silicon Valley for the first time

9:15: Where did the idea for Hippo Insurance come from? 

14:07: Overcoming the challenges a heavily regulated market brings

16:30: Realizing this was a business and not just an experiment 

18:51: Obtaining the first 100 customers 

22:13: Early pushback from investors and employees 

25:37: Breaking Hippo Insurance down into two chapters

28:55: Building the culture

36:51: Showing up for customers during the 2020 California wildfires 

41:54: The Sprint