From surgeon to psychiatrist, Bitcoin investor to billion-dollar crypto brokerage founder, Dr. Prash Puspanathan has lived one of the most unconventional founder journeys in tech. After co-founding and scaling Caleb & Brown into a global crypto powerhouse, later acquired by SwiftX in 2025, Dr. Prash is now pioneering the future of mental health with Enosis Therapeutics, using VR to transform psychedelic-assisted therapy integration.

In this episode of Perspective X, Dr. Prash shares how a single psilocybin experience completely reshaped his worldview, steering him away from surgery and into psychiatry, entrepreneurship, and eventually, crypto. He reveals the parallels between fiscal freedom in decentralized finance and cognitive freedom in mental health, the scrappy early days of arbitrage trading, and the challenges of scaling a white-glove brokerage to serve high-net-worth clients worldwide.

We also dive into the future of psychedelic medicine, why integration is the “real work,” how technology can lower costs and increase access, and why prevention, not just treatment, will define the next era of mental health. From paradigm-shifting psychedelics to building billion-dollar ventures, this is a conversation about liberation, of thought, finance, and human potential.

00:00 – Intro: Dr. Prash’s unconventional founder journey

02:00 – From surgery to psychiatry: psychedelics as a turning point

06:30 – The transformative psilocybin experience and shifting paradigms

10:30 – Understanding psychedelic therapy and integration work

16:00 – Why psychedelics challenge power structures and cultural norms

22:00 – Fiscal freedom and cognitive freedom: psychedelics and Bitcoin

30:00 – Founding Caleb & Brown and building a billion-dollar brokerage

37:00 – Global scaling, high-net-worth clients, and leadership transitions

42:00 – Preparing for acquisition: the 9-month journey to SwiftX

50:00 – Running a dual life as psychiatrist and founder

55:00 – Enosis Therapeutics: VR-powered integration for psychedelic therapy

01:02:00 – Building tools for patients, therapists, and the future of mental health

01:10:00 – The vision for a psychological digital twin

01:15:00 – Psychedelics in the next 10–50 years: from treatment to prevention

01:20:00 – Translating research into real-world impact and future mission

💰 Caleb & Brown – Global crypto brokerage: https://calebandbrown.com

🩺 Enosis Therapeutics – Tech for psychedelic-assisted therapy: https://www.enosistherapeutics.com/

👤 Dr. Prash on LinkedIn: https://www.linkedin.com/in/drprash/

Vanta:

Vanta is the all-in-one solution for startups to become compliant quickly and build a security foundation with ease.

Startup customers get $1000 off Vanta at

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Mighty Partners:

Mighty Partners is a growth lender supporting ambitious Australian companies with bespoke debt funding solutions.

Day One listeners are invited to book a complimentary venture debt consultation with Mighty Partners. To schedule your call, simply follow the link and mention "Day One Free Consult"

dayone.fm/mighty

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Mentioned in this episode:

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Episode Summary

Yotam Rosenbaum never planned to be a startup founder, let alone one of Australia’s most active investors in Y Combinator companies. He started out as a musician, marketing his own band in Los Angeles, until the frustration of promoting music online became the spark for building Earbits, a platform once described as “Google AdWords for music.” What began on a traffic-jammed freeway turned into a five-year journey through Y Combinator, product-market chaos, and a successful exit.

Since then, Yotam has backed over 400 YC startups, built one of the only Australian-led funds inside the program, and helped founders at home think far beyond local markets. He reflects on what actually matters at the earliest stages, why founder relationships trump early traction, and how to spot the quiet signals of a breakout team. There’s also a reality check for anyone raising capital: most investors won’t give you a clear no, and that’s the real cost.

From Craigslist drum lessons to portfolio unicorns, Yotam’s story is anything but typical. But it’s proof that trusting your sense of direction, without needing the whole map, can still get you somewhere remarkable.

Time Stamps

00:01:17 – Embracing Uncertainty: Yotam’s Philosophy on Direction Without a Map

00:06:41 – From Funk Band to Founder: The Origins of Earbits

00:11:05 – The Aha Moment: Building the Google AdWords for Music

00:14:58 – Joining Y Combinator: Early Traction & Getting In

00:20:04 – Life at YC: Feeling Out of Place, Finding Belonging

00:24:29 – Investing in 400+ YC Startups: How It Started Post-Exit

00:31:19 – Moving to Australia: The Hot DesQ Bet That Paid Off

00:36:35 – Comparing Ecosystems: SF vs Brisbane Startup Mindsets

00:41:09 – The Importance of Community: No Founder Builds Alone

00:45:39 – The 77 Partners Venture Challenge: Who It’s For

00:50:24 – What Investors Look For (It’s Not Just Revenue)

01:03:01 – How Founders Can (And Should) Think About AI

Resources Mentioned

🥇 First Peak Ventures - https://www.linkedin.com/company/first-peak-ventures/

🤝 77 Partners – http://www.77partners.vc/

🙋🏻‍♂️ Yotam Rosenbaum on LinkedIn – https://www.linkedin.com/in/yotamrosenbaum/

👂🏻 Earbits – https://www.earbits.com/

Vanta:

Vanta is the all-in-one solution for startups to become compliant quickly and build a security foundation with ease.

Startup customers get $1000 off Vanta at

dayone.fm/vanta/pauline

Mighty Partners:

Mighty Partners is a growth lender supporting ambitious Australian companies with bespoke debt funding solutions.

Day One listeners are invited to book a complimentary venture debt consultation with Mighty Partners. To schedule your call, simply follow the link and mention "Day One Free Consult"

dayone.fm/mighty

To learn more, join our newsletter to be notified of new Perspective X episodes and upcoming shows.

Mentioned in this episode:

Vanta_PX_May 2025

Mighty Partners_PX_May 2025

Ricky Sevta isn’t afraid of hard truths, or hard problems. As the former Chief Revenue Officer at simPRO, Ricky helped scale the company from $10M to $100M ARR, led a $550M capital raise, and expanded the business into global markets. Now, as CEO of Deep Space and a partner at Venture On, he’s back at the beginning, building again.

In this episode, Ricky shares the behind-the-scenes realities of scaling a company beyond product-market fit, why founders underestimate the cost of growth, and the personal sacrifices that come with chasing unicorn status. He also reveals how Deep Space is tackling fragmented workflows in construction with modern, AI-powered software, and why pricing, timing, and hiring are all about ruthless clarity.

From celebrating too little, to learning how to protect time with family, Ricky unpacks the emotional toll of leadership, how to spot premature market entry, and why customer obsession isn’t optional, it’s survival.

02:00 – Ricky’s transition from engineer to CRO and global scale-up leader

05:30 – The messy middle: scaling simPRO from $10M to $100M ARR

08:20 – Building structure into chaos: onboarding, playbooks, and the “Lego” method

11:00 – Why product-market fit is never static—especially across geographies

13:30 – Market trumps team: Ricky’s framework for evaluating expansion risks

16:50 – Don’t skip the customer: 40% of Ricky’s time was spent on the ground

19:00 – What “Chief Revenue Officer” really meant at simPRO

22:00 – The traits Ricky looks for when hiring early-stage startup leaders

24:40 – The emotional cost of startup life: family, friendships, and isolation

28:00 – Why founders often create businesses to fix something in themselves

33:00 – Leaving simPRO: starting again with Deep Space and Venture On

37:00 – Building in public and launching an AI-powered construction OS

43:10 – Why the construction industry isn’t “behind”—it’s been underserved

50:00 – Deep Space’s AI agent “Kai” and the platform’s competitive edge

56:00 – How modern architecture unlocks personalization and speed

01:02:00 – Ricky’s take on AI disruption, job loss, and market overreactions

01:10:00 – Pricing strategy: why Deep Space chose fixed pricing over revenue-based models

01:16:00 – Signs it’s time to enter a new market (hint: it’s not when you are ready)

01:22:00 – Product feedback loops and building a customer-driven roadmap

01:27:00 – Celebrating small wins and creating a culture of recognition

01:30:00 – Ricky on joy, drive, and why he’d do it all again—burnout and all

🔧 Deep Space – AI construction management platform https://www.deepspacegroup.ai/

👤 Ricky Sevta on LinkedIn https://www.linkedin.com/in/rickysevta/

Vanta:

Vanta is the all-in-one solution for startups to become compliant quickly and build a security foundation with ease.

Startup customers get $1000 off Vanta at

dayone.fm/vanta/pauline

Mighty Partners:

Mighty Partners is a growth lender supporting ambitious Australian companies with bespoke debt funding solutions.

Day One listeners are invited to book a complimentary venture debt consultation with Mighty Partners. To schedule your call, simply follow the link and mention "Day One Free Consult"

dayone.fm/mighty

To learn more, join our newsletter to be notified of new Perspective X episodes and upcoming shows.

Mentioned in this...