This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________
Aleks Spaseska is the CEO of Kmart Group, an A$11.8 billion (US$8 billion) retail giant behind Kmart, Target and the global Anko brand, operating 445 stores with over 48,000 employees. This is a rare in-depth interview with Aleks.

In this rare public conversation, Aleks Spaseska joins Vidit to share how she went from struggling to find her confidence at school to becoming CEO of one of the region’s largest retailers. She reveals the career move that changed everything, how she returned from maternity leave into a bigger leadership role, and what really helped her stand out from her peers.

They also explore the realities of running a retail giant, the leadership mistakes that shaped her, why she never had a 10-year career plan, and how her childhood continues to influence the decisions she makes as CEO.

Please enjoy exploring your curiosity.

_______

Get in touch with us via email at contact@curiositycentre.com

Join our stable of commercial partners including the Australian Government, Google, KPMG,, Allens, Macquarie Capital, Xero, JP Morgan and more. 

Show notes and more episodes here [https://curiositycentre.com/the-high-flyers-podcast/ep-285-aleks-spaseska-managing-director-kmart-group]

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Get in touch with our Founder and Host, Vidit Agarwal directly here [https://www.viditagarwal.org/]

Contact us via our website [https://www.curiositycentre.com/#wf-form-Contact-Form]

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

TIMESTAMPS


00:00 Meet Aleks Spaseska
02:20 Why store managers are underrated leaders
05:50 Growing up in Macedonia
08:45 No English
10:15 Why she never planned her career
11:15 How childhood shaped her view of affordability
13:10 From university to a finance PhD
17:45 The career move that changed everything
20:50 Lessons from her early Wesfarmers years
25:30 Taking uncomfortable career risks
28:00 Transforming Target's business
33:50 Learning empathy as a leader
37:15 Maternity leave, relocation and COVID
39:15 Making decisions without rigid plans
41:20 How Kmart operates within Wesfarmers
46:00 From CFO to CEO of Kmart
49:10 The Anko business model and global expansion
54:00 Kmart's next chapter of growth
56:40 Rapid fire round

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The High Flyers Podcast [https://www.thehighflyerspodcast.com/]features in-depth interviews with the world’s most influential figures in business, tech, finance, government and sport. Launched in 2020, it has ranked in the global top ten for past three years, with listeners in 27 countries and over 200+ episodes released, and featured in Forbes, Daily Telegraph, and at SXSW.

Our guests include -- Malcolm Turnbull (Prime Minister of Australia), Keith Rabois (Managing Director, Khosla Ventures), Jason Collins (Head of

#285 Aleks Spaseska: Kmart's CEO on Her Macedonian Upbringing, Taking Uncomfortable Career Risks and Why Retail Is Rewarding

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

Venky Ganesan is a Partner at Menlo Ventures, one of Silicon Valley’s oldest venture capital firms, where he has helped lead its push into AI and backed companies including Anthropic, Abnormal AI and Palo Alto Networks. He has spent 20+ years in venture capital, after starting his career as an entrepreneur and co-founding Trigo Technologies, which was acquired by IBM in 2004.

In this rare public conversation, Venky joins Vidit to unpack a journey that began in India before he moved alone to rural Washington State at 16. He shares the culture shock of arriving in America, working through college, choosing a $39,000 McKinsey job over a far more lucrative offer, and eventually becoming an entrepreneur — co-founding Trigo Technologies and selling the company to IBM in 2004.

They also explore Venky’s 20+ years in venture capital, from backing Palo Alto Networks early in its journey to becoming a Partner at Menlo Ventures and helping drive the firm’s push into AI. Venky shares what separates good founders from great ones, why “propensity for action” has become one of his strongest signals, how he thinks about position sizing and why VCs often end up with more money in their worst companies than their best. He also unpacks today’s extraordinary AI market, investing in Anthropic, and why he believes the industry is moving from innovators to “imitators and idiots.”  

Venky reflects on the role his wife has played in his life, the stroke that nearly killed him and changed his perspective, what more than two decades of investing have taught him about ambition, and more.

Please enjoy exploring your curiosity.

_______

Get in touch with us via email at contact@curiositycentre.com

Join our stable of commercial partners including the Australian Government, Google, KPMG,, Allens, Macquarie Capital, Xero, JP Morgan and more. 

Show notes and more episodes here [https://curiositycentre.com/the-high-flyers-podcast/ep-284-venky-ganesan-partner-menlo-ventures]

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Get in touch with our Founder and Host, Vidit Agarwal directly here [https://www.viditagarwal.org/]

Contact us via our website [https://www.curiositycentre.com/#wf-form-Contact-Form]

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

TIMESTAMPS


01:17 — The 15-year-old who talked his way into a job
03:21 — Growing up in India with big ambitions
08:08 — An unexpected lesson from Nelson Mandela
10:05 — Leaving India alone at 16
14:10 — Why technology became his path to freedom
22:41 — McKinsey, entrepreneurship and selling to IBM
31:13 — From founder to venture capitalist
39:57 — The signal Venky looks for in great founders
44:02 — How he backed Palo Alto Networks early
47:00 — Reinventing Menlo for the AI era
53:14 — AI’s “innovators, imitators and idiots”
59:25 — The most disorienting market of his career


#284 Venky Ganesan: Menlo Ventures Partner on early Anthropic investment and moving from India to rural America at 16

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

David Schneider is a General Partner at Coatue, where he co-leads the firm’s Growth Fund. Previously, he was President at ServiceNow, helping scale the company from roughly $100M to $5B in revenue, after helping take another software company in Data Domain from zero customers to more than $1B in revenue. David is widely regarded as one of Silicon Valley’s most successful go-to-market, sales, revenue and business building executives of all time.

In this rare public conversation, David joins Vidit to unpack a career spent building some of enterprise software’s defining companies. He shares how he was initially rejected by Data Domain for not being “aggressive enough”, only to join when it had zero customers and around 18 employees and help scale it beyond $1 billion in revenue — revealing the intensity, hiring philosophy and relentless focus on execution that shaped him as a leader.  

They also explore David’s decade at ServiceNow, where he helped scale the business from roughly $100 million to $5 billion, what he learned working alongside legendary CEO Frank Slootman, and the painful customer failure that fundamentally changed how he thought about leadership. David then opens up about leaving operating at the height of his career to become a General Partner at Coatue, where he now co-leads its Growth Fund, and the surprisingly difficult transition from being the person making decisions to the investor sitting beside the founder. Along the way, he reflects on building exceptional sales teams, spotting future leaders, the future of enterprise go-to-market, flying 250,000–350,000 miles a year, the impact that ambition had on his family, and why curiosity has remained a constant throughout his life.

Please enjoy exploring your curiosity.

_______

Get in touch with us via email at contact@curiositycentre.com

Join our stable of commercial partners including the Australian Government, Google, KPMG,, Allens, Macquarie Capital, Xero, JP Morgan and more. 

Show notes and more episodes here [https://curiositycentre.com/the-high-flyers-podcast/ep-283-david-schneider-cotaue-growth-fund-co-lead]

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Get in touch with our Founder and Host, Vidit Agarwal directly here [https://www.viditagarwal.org/]

Contact us via our website [https://www.curiositycentre.com/#wf-form-Contact-Form]

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

TIMESTAMPS

00:00 – Left Field Questions
01:24 – The founder David is betting on
04:01 – Growing up in Silicon Valley before the boom
08:25 – How David became obsessed with winning
24:45 – Rejected by Data Domain for not being “aggressive enough”
28:40 – From zero customers to a billion-dollar business
40:00 – What David learned working with Frank Slootman
50:23 – The customer failure David never forgot
52:25 – How David helped scale ServiceNow from $100M t

#283 David Schneider: Scaling ServiceNow from $100M to $5B, Frank Slootman learnings, Left-Field Questions and Co-Leading Coatue’s Growth Fund

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

Paul Grosmann is the CEO of R.M.Williams, the 94-year-old heritage bootmaker whose handcrafted leather boots have become one of Australia’s most recognisable cultural exports, worn from the outback to boardrooms around the world. He is leading the next phase of growth for the business, which generates hundreds of millions of dollars in annual revenue, expanding it as a global premium brand while preserving its manufacturing roots in Adelaide. Before R.M.Williams, Paul built an unusually international career across PwC and McKinsey, before leading strategy and digital growth for Nike in Greater China.

In this rare public conversation, Paul joins Vidit to unpack an unusually global career, from Sydney to New York and China, including quitting his job and spending a year learning Mandarin to earn a role with McKinsey in Shanghai. He shares what he learned working inside Brett Blundy’s private business group, how he pitched his way into Nike and helped lead its retail and digital growth across Greater China, and why decision-making changes across public companies, private businesses and founder-led organisations.

They also explore Paul’s return to Australia to lead R.M.Williams, the 94-year-old heritage brand whose handcrafted boots have become one of the country’s most recognisable cultural exports. Paul explains how the company has doubled its production capacity and created 350 Australian jobs, while expanding online, attracting younger and female customers, and building an international retail presence through an unconventional UK strategy. Along the way, he reflects on cold emails, considered decision-making, living across cultures, balancing ambition with family, and the role his wife Sophie has played throughout the journey.

Please enjoy exploring your curiosity.

_______

Get in touch with us via email at contact@curiositycentre.com

Join our stable of commercial partners including the Australian Government, Google, KPMG,, Allens, Macquarie Capital, Xero, JP Morgan and more. 

Show notes and more episodes here [https://curiositycentre.com/the-high-flyers-podcast/ep-282-paul-grosmann-ceo-rm-williams]

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Get in touch with our Founder and Host, Vidit Agarwal directly here [https://www.viditagarwal.org/]

Contact us via our website [https://www.curiositycentre.com/#wf-form-Contact-Form]

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

TIMESTAMPS

00:00 Cold emails
04:32 Growing up in a loud Italian family
07:35 Becoming a global citizen
13:55 Quitting work to learn Mandarin
18:29 Learning to operate in China
20:31 Choosing mentors over promotions
22:11 Paul’s cold-email playbook
23:57 The leadership power of pausing
27:09 Why Paul left McKinsey
28:57 Learning retail from Brett Blundy
34:28 Public versus private companies
40:39 Rising rapidly at Nike China
45:3

#282 Paul Grosmann: R.M.Williams CEO on learning Mandarin, cold emails, rising through Nike and how to listen well

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

Mike Vernal is a General Partner at Conviction and one of Silicon Valley’s most respected operator-turned-investors. He joined Facebook very early, spent eight years there working closely with Mark Zuckerberg and ultimately became VP of Product and Engineering, before becoming a partner at storied venture capital firm Sequoia Capital, where he backed companies including Notion, Rippling, Clay and Statsig.

In this conversation, Mike joins Vidit to unpack the journey from Microsoft to joining Facebook when it was still only a few hundred people, helping scale it through one of the most important periods in technology, and later becoming a partner at Sequoia before joining Conviction. He shares what he learned working closely with Mark Zuckerberg, why Facebook’s obsession with speed became such an advantage, how he learned to spot exceptional founders, and why ambition remains one of the traits he values most.

They also explore why Mike believes people risk “overfitting” to a job after seven years, what Sequoia taught him about great businesses, why he came back to venture after some of the most enjoyable years of his life with his family, and what changes when the cost of creating software starts approaching zero. Along the way, Mike shares the habits, quirks and principles behind his reputation as a “nerd’s nerd”, from obsessive curiosity and inbox zero to the belief that the best leaders make the people around them better.

Please enjoy exploring your curiosity.

_______

Get in touch with us via email at contact@curiositycentre.com

Join our stable of commercial partners including the Australian Government, Google, KPMG,, Allens, Macquarie Capital, Xero, JP Morgan and more. 

Show notes and more episodes here [https://curiositycentre.com/the-high-flyers-podcast/ep-281-mike-vernal-partner-convinction]

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Get in touch with our Founder and Host, Vidit Agarwal directly here [https://www.viditagarwal.org/]

Contact us via our website [https://www.curiositycentre.com/#wf-form-Contact-Form]

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

TIMESTAMPS

00:00 — The Nerd’s Nerd
04:00 — Growing Up in New York
08:00 — Power, Internet and Caffeine
13:00 — Working at a Startup in High School
14:00 — Why Harvard Became the Goal
18:00 — Meeting His Wife
24:00 — What Microsoft Taught Him
31:00 — Why Strategy Can Go Wrong
33:00 — How Facebook Built High-Impact Teams
37:00 — The Moment Facebook Felt Different
43:00 — Facebook’s Speed Advantage
49:00 — Why Mike Left Facebook
54:00 — Why Sequoia
56:00 — Learning What Makes a Great Business
59:00 — Why He Doesn’t Take Notes
01:01:00 — What Mike Looks for in Founders
01:07:00 — Leaving Sequoia
01:09:00 — Why He Joined Conviction
01:14:00 — How Mike Spots What’s Next
01:16:00 — When Software Costs Approach Zero

#281 Mike Vernal: Early Facebook Engineer with Zuck to VC at Sequoia to Conviction, What’s Real in AI | The Nerd’s Nerd

Welcome to the 14th episode in our special series with the Australian Government and their Centre for Australia–India Relations (CAIR), spotlighting the growing Australia–India relationship across technology, business, media, culture and sport.

Other guests in this series include BHP's CFO Vandita Pant, Bank of America's Head of Capital Commitments Gautam Chari, Austrade's GM for South Asia Mukund Narayanamurti, Renowned Music Composer Tushar Apte, Australia's High Commissioner to India Philip Green, MUFG's CEO Vivek Bhatia, Australia's Secretary of Foreign Affairs Peter Varghese, NAB's EGM Sweta Mehra, Deputy Secretary of Australia's Home Affairs Brendan Dowling, Orica's CEO Sanjeev Gandhi, Sports Journalist Bharat Sundaresan, Cricket Legend Lisa Sthalekar and CAIR's CEO, Ryan Neelam, reflecting the breadth of Indian-Australian leaders at the most senior levels.

________

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

Get in touch with us via email at contact@curiositycentre.com

Join our stable of commercial partners including the Australian Government, Google, KPMG,, Allens, Macquarie Capital, Xero, JP Morgan and more.

________

Amit Singh is Managing Partner of Mandala, a global economics, data and policy research firm. He has advised three Australian Prime Ministers, served as Uber’s Global Head of Economic Policy in San Francisco, and more. Today, he leads Mandala and serves on several prominent government and public-policy boards.

In this conversation with Vidit, Amit shares his journey from growing up amid political instability in Fiji and moving to Australia as a teenager, to running a $20 million organisation with 200 employees at just 21 — before going on to work at the highest levels of Australian government.  

He reflects on going from Freehills to Kevin Rudd’s office in the space of two days, subsequently working for Julia Gillard and briefly Anthony Albanese, and the experience of technically losing his job five times during his political career. Amit also shares the equal-pay decision he is proudest of, which delivered a 23–45% pay increase for 150,000 predominantly female care workers.  

Amit also explains why he left government for technology, what moving to San Francisco and working at Uber taught him about ambition and taking risks, and how those experiences ultimately led to building Mandala as a globally focused economics and policy firm.  

They also explore Amit’s Fijian-Indian identity, why he believes the Australia–India economic relationship remains underdone despite decades of intent, the opportunity across technology, AI and services, and why changing Australians’ understanding of modern India could unlock a much deeper relationship.  

Please enjoy exploring your curiosity.

______

Get in touch with us via email at contact@curiositycentre.com

Join our stable of commercial partners including the Australian Government, Google, KPMG,, Allens, Macquarie Capital, Xero, JP Morgan and more. 

Show notes and more episodes here [https://curiositycentre.com/the-high-flyers-podcast/ep-280-amit-singh-managing-partner-mandala]

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Get in touch with our Founder and Host, Vidit Agarwal directly

#280 Amit Singh: Fijian-Indian Roots, Inside Two Prime Ministers’ Offices & Why He Built His Own Research Firm

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

Ryan Beiermeister is a Partner at Founders Fund, one of the world’s leading venture capital firms. Before becoming an investor, she held senior roles at three of the most consequential technology companies of the past decade: VP at OpenAI leading AI safety work, Product Director at Meta across election integrity and social issues, and VP at Palantir, where she helped lead development of Gotham. At College, Ryan was the #1 ranked college policy debater in the US and won top speaker at the 2012 national championship, becoming only the fourth woman since 1946 to do so.

In this conversation, Ryan joins Vidit to unpack the unconventional path from Houston and elite college debate to Palantir, Meta, OpenAI and now Founders Fund, including why Palantir took a chance on her at 22, what she learned building products for governments and billions of users, and why she believes there is still “no replacement for human judgement” in the age of AI.

They also explore the risks of building technology and simply “throwing it over the wall”, the developmental impact of AI on young people, what makes humans uniquely valuable in an increasingly automated world, and Ryan’s early lessons from making the leap from operator to venture capitalist.

Please enjoy exploring your curiosity.

_______

Get in touch with us via email at contact@curiositycentre.com

Join our stable of commercial partners including the Australian Government, Google, KPMG,, Allens, Macquarie Capital, Xero, JP Morgan and more. 

Show notes and more episodes here [https://curiositycentre.com/the-high-flyers-podcast/ep-279-ryan-beiermeister-partner-founders-fund]

Follow us on LinkedIn, [https://www.linkedin.com/company/thehighflyers]Twitter [https://twitter.com/vidags10]and Instagram [https://www.instagram.com/thehighflyerspodcast]

Get in touch with our Founder and Host, Vidit Agarwal directly here [https://www.viditagarwal.org/]

Contact us via our website [https://www.curiositycentre.com/#wf-form-Contact-Form]

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

TIMESTAMPS

 * 01:28 From Palantir to Founders Fund
 * 04:00 The mentor who changed everything
 * 07:05 Growing up in Houston
 * 10:00 Feeling different at an elite school
 * 12:00 Why high-performing women are different
 * 14:00 Nolan Ryan
 * 17:00 When debate became her superpower
 * 20:00 Why Meta used her whole brain
 * 22:00 Books, empathy & social justice
 * 25:00 No master plan 
 * 27:00 How Palantir bet on a debate champion
 * 32:00 From user empathy to building Gotham
 * 34:00 Learning to double down on strengths
 * 37:00 Trae Stephens
 * 41:00 Breaking the VC pattern-recognition playbook
 * 41:40 Ca

#279 Ryan Beiermeister: Founders Fund's Partner on Building for Billions, Human Judgement & How Debate Changed Her Life

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

Ellen DaSilva is the Founder and CEO of Summer Health, the pediatric healthcare company that served 30,000+ families before being acquired by Doctronic in 2026. Earlier, she was employee #8 at Hims & Hers and worked at Twitter during its hyper growth years. She is an active angel investor and Sequoia Scout, and earned her MBA with Distinction from Harvard Business School.

In this conversation, Ellen joins Vidit to unpack the ambition behind her extraordinary career, the leap from Wall Street to scaling Twitter during its hyper gowth years, why she nearly became a Hims competitor before joining as employee #8, and what happened when she finally took the founder leap with Summer Health.

They also explore how consumer software has changed, what makes great companies feel “inevitable”, why Ellen is “incapable of turning off founder mode”, and the philosophy behind living life on “maximum mode” and lots more. 

Please enjoy exploring your curiosity.

_______

Get in touch with us via email at contact@curiositycentre.com

Join our stable of commercial partners including the Australian Government, Google, KPMG,, Allens, Macquarie Capital, Xero, JP Morgan and more. 

Show notes and more episodes here [https://curiositycentre.com/the-high-flyers-podcast/ep-278-ellen-dasilva-ceo-founder-summer-health]

Follow us on LinkedIn, [https://www.linkedin.com/company/thehighflyers]Twitter [https://twitter.com/vidags10]and Instagram [https://www.instagram.com/thehighflyerspodcast]

Get in touch with our Founder and Host, Vidit Agarwal directly here [https://www.viditagarwal.org/]

Contact us via our website [https://www.curiositycentre.com/#wf-form-Contact-Form]

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

TIMESTAMPS

00:00 Ellen’s “hot take” on consumer AI
02:00 From Barclays to selling Summer Health
05:00 Growing up ambitious in New York
09:00 The family behind Ellen’s drive
11:00 “CEO of Coca-Cola” at age five
13:00 Politics, Bloomberg & an early obsession with change
15:00 Why Ellen studied English literature
18:00 Raising three intensely curious kids
19:00 China vs Wall Street
23:00 “I knew I was going to marry him”
26:00 Discovering tech from a Wall Street desk
29:00 The 10-day leap from Barclays to Twitter
31:00 Scaling Twitter during hypergrowth
33:00 Why “every job becomes sales”
35:00 How Twitter shaped Summer Health
38:00 HBS, ambition & “colouring outside the lines”
42:00 How Ellen spots exceptional companies early
45:00 The startup she nearly built before Hims
47:00 employee #8 at Hims to IPO
48:00 Building healthcare like consumer software
49:00 Why Summer Health removed the interface
51:00 Why text-based products may win
52:00 What Ellen would build next
54:00 Why Summer Health sold to Doctronic
57:00 Ellen’s fundraising playbook
01:02:00 The 5 people in her "hall of fame" room
01:08:00 The hardest period of her career
01:11:00 “I’m incapable of turning off founder mod

#278 Ellen DaSilva: Scaling Twitter, Hims Employee #8, Sequoia Scout & building Summer Health on “Maximum Mode”

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

Dr. Shiv Rao is the Co-Founder and CEO of Abridge, one of the world’s leading healthcare AI companies, turning clinician-patient conversations into clinical intelligence across 300+ health systems and 100M+ conversations annually. A practising cardiologist, Shiv previously worked across healthcare technology and investing at UPMC before founding Abridge in 2018.

In this rare in-depth conversation, Shiv joins Vidit to unpack his unconventional path: moving from Pittsburgh to India at nine, skateboarding, programming synthesizers, selling records in Japan and nearly quitting medical school before becoming a cardiologist.

He shares how a seemingly perfect career across medicine, technology and investing left him “incredibly restless”, eventually leading to Abridge. But success was far from immediate: Shiv spent nearly four years as a “languishing founder” before generative AI arrived, “the sky just opened up”, and Abridge made its pivotal move into enterprise healthcare.

They also explore why “pressure makes diamonds”, the family sacrifices behind building when “every minute matters”, what changes when a company passes 500 people, why Shiv still practises medicine, and what he’s learned from unlikely influences including Jensen Huang and Rick Rubin.

Please enjoy exploring your curiosity.

________

Get in touch with us via email at contact@curiositycentre.com

Join our stable of commercial partners including the Australian Government, Google, KPMG,, Allens, Macquarie Capital, Xero, JP Morgan and more. 

Show notes and more episodes here [http://curiositycentre.com/the-high-flyers-podcast/ep-277-shiv-rao-ceo-co-founder-abridge]

Follow us on LinkedIn, [https://www.linkedin.com/company/thehighflyers]Twitter [https://twitter.com/vidags10]and Instagram [https://www.instagram.com/thehighflyerspodcast]

Get in touch with our Founder and Host, Vidit Agarwal directly here [https://www.viditagarwal.org/]

Contact us via our website [https://www.curiositycentre.com/#wf-form-Contact-Form]

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

________

TIMESTAMPS

00:00 Meet Shiv Rao
02:00 Living on planes 
04:55 Xero
07:00 Pittsburgh and India
12:00 Identity, India & belonging
17:00 Skateboarding, music & creativity
19:00 The moment that led Shiv to medicine
23:00 Selling records in Japan
25:00 Nearly quitting medical school
28:00 Medicine’s complicated relationship with technology
30:00 Teaching himself to code & early product-market fit
35:00 Why “pressure makes diamonds”
39:00 Medicine → healthcare investing
44:00 Leaving the “dream job” to build Abridge
48:00 Family sacrifice & the reality of building
50:00 Why “every minute matters” in AI
54:00 Abridge’s years as a “languishing” startup
59:00 When “the sky just opened up”
1:01:00 Abridge’s YOLO move into enterprise
1:03:00 The first customer “Love Stories”
1:10:00 Why enterprise healthcare is so defensible
1:15:00 Building AI that enterprises can’t

#277 Shiv Rao: Abridge’s CEO on Skateboarding, “Languishing” Founder Pressure & Reinventing How Doctors Work

This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

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John Willett is the Co-Founder and Chief Operating Officer of Rogo, one of the fastest-growing AI companies in global finance, used by leading institutions including Lazard, Jefferies, Rothschild & Co, Moelis and Nomura. Rogo has raised more than $300 million from investors including Kleiner Perkins, Sequoia, Thrive and Khosla, was valued at $2 billion in 2026, and John now leads its expansion across Europe and APAC.

In his first in-depth interview ever, John joins Vidit to tell the story behind Rogo and the person behind the company. He reflects on growing up in Connecticut in a family of engineers, being academically far ahead of his peers, meeting co-founder Gabe Stengel at Princeton, and experimenting with AI for finance years before ChatGPT made the category obvious.

John shares how early investor Kevin Ryan convinced them to quit investment banking and go all in, why Rogo spent its first two years with little external validation, and how ChatGPT changed enterprise demand almost overnight. He also explains how Lazard became the first major customer, what it took to earn the trust of global banks, and how Rogo evolved from an early product into a platform tackling some of finance’s most complex workflows.

They also unpack John and Gabe’s co-founder dynamic, why Gabe became CEO, how Rogo recruits former bankers into operating roles, and what John has learned scaling the company from roughly 40 to 200 people while building out Europe and APAC.

Please enjoy exploring your curiosity.

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This episode is supported by Xero, helping businesses use AI with more control through JAX, its in-platform AI finance partner. Get 90% off your plan for your first 6 months at xero.com/highflyers [http://xero.com/highflyers]. 

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TIMESTAMPS

00:00 – The Real John Willett
04:33 – Xero
06:01 – The Family of Engineers Behind John
11:11 – Meeting Gabe at Princeton
12:22 – The Idea Before Rogo
17:16 – Building AI Before ChatGPT
18:46 – The Investor Who Told Them to Quit Banking
20:11 – Rogo’s First Fundraising Deck
24:31 – Two Years Nobody Wanted Rogo
27:16 – The ChatGPT Inflection Point
29:16 – Landing Rogo’s First Major Customer
34:11 – When Enterprise AI Started to Click
38:11 – Why Big-Name Customers Matter
43:10 – Deciding Who Should Be CEO
45:22 – Convincing Bankers to Join a Startup
50:09 – US vs Europe vs APAC
55:04 – Scaling Rogo From 40 to 200+People
01:00:04 – Becoming a Be

#276 John Willett: Rogo’s COO on Princeton, Being Ignored for Years to Winning the World’s Biggest Banks

Vidit Agarwal (@vidag) · Zencastr

Vidit Agarwal (@vidag)

Thanks to you, we rank in the top 10% most shared podcasts globally, with listeners in 27 countries. With host Vidit Agarwal, re-imagine the traditional high flyer and celebrate relatable role models, and their journeys from their sunrise to today, across 40+ walks of life around the world! Contact us anytime via: Website: www.curiositycenter.xyz/podcast Twitter: https://twitter.com/vidags10 Linkedin: https://www.linkedin.com/in/viditag/ IG: https://www.instagram.com/thehighflyerspodcast/

The High Flyers Podcast with Vidit Agarwal