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.

Time Stamps

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

Resources

💰 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/

Sponsors:

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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/

Sponsors:

Perspective X is supported by our wonderful sponsors:

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"

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Perspective X is part of Day One.

Day One helps founders and startup operators make better business decisions more often.

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

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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.

Time Stamps

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

Resources Mentioned

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

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

Sponsors:

Perspective X is supported by our wonderful sponsors:

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

Perspective X is part of Day One.

Day One helps founders and startup operators make better business decisions more often.

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

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Paul Stovell, founder and CEO of Octopus Deploy, shares his journey from coding side projects in a Brisbane library to building a $100M+ ARR global business in the competitive world of DevOps. Paul reveals how a relentless focus on product excellence, profitability, and customer value enabled Octopus Deploy to scale without relying on constant investor funding, becoming one of Australia’s most successful software companies.

He delves into the benefits (and pitfalls) of building with transparency, why he rejected Silicon Valley’s growth-at-all-costs mindset, and how he structured Octopus Deploy for sustainable, long-term growth. Paul also unpacks the personal challenges of balancing family, co-founding with his wife, and maintaining passion for building, plus why he’s still at the helm despite the inevitable burnout moments.

If you’re a founder, operator, or investor curious about bootstrapping vs. fundraising, scaling a product-led SaaS, or maintaining healthy relationships while building an empire, this episode is packed with raw insights.

Time Stamps

02:20 – Building Octopus Deploy: From Brisbane library to $100M ARR

05:00 – Bootstrapping and turning down a $400K early acquisition offer

08:30 – Co-founding with your spouse: Paul and Sonya’s partnership story

12:10 – Creating a contrarian culture: Remote-first before it was trendy

15:45 – How Australia’s startup ecosystem evolved from 2012 to today

20:30 – Becoming profitable from day one: The mindset behind sustainable growth

26:00 – Facing down Microsoft: Pivoting to survive industry giants

31:10 – Why transparency and building publicly were key growth levers

36:50 – Scaling to 100 employees without losing the original vision

43:00 – Raising $172M from Insight Partners (without needing the money)

50:10 – The realities of taking on investors: How Paul views venture capital

57:00 – Navigating burnout and founder stress while scaling globally

01:04:20 – Hiring mistakes, culture clashes, and leadership lessons learned

01:12:45 – Goal-setting without rigid KPIs: Paul’s unconventional strategy

01:22:00 – Personal life balance: Family, renovating classic cars, and keeping perspective

01:29:30 – What’s next for Octopus Deploy: Staying independent and profitable

Resources Mentioned

🐙 Octopus Deploy – https://octopus.com

📖 Octopus Public Handbook – https://handbook.octopus.com

📊 Octopus Investor Relations – https://ir.octopus.com

👤 Paul Stovell’s LinkedIn – https://www.linkedin.com/in/paulstovell

Sponsors:

Perspective X is supported by our wonderful sponsors:

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

Perspective X is part of Day One.

Day One helps founders and startup operators make better business decisions more often.

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

Mentioned in this episode:

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Bryony Cole is the founder of Future of Sex and Sex Tech School, and a global authority on the intersection of sexuality and technology. In this episode, she shares how she left a career in corporate tech to build the sex tech industry from the ground up.

She opens up about the personal rebellion that drove her early experiments, from living in a forest commune to launching a podcast that evolved into a movement. Bryony unpacks what it really took to pioneer a taboo space – from getting censored and locked out of banks, to renting out her apartment to fund live events.

The conversation also explores how AI, loneliness, and digital saturation are reshaping intimacy and identity. Bryony shares her view on what’s coming next – not just in sex tech, but in how people relate to themselves, each other, and the tools around them. She calls it the “Future of Self.”

For founders building against the grain, creators navigating cultural friction, or anyone questioning what connection looks like in a hyper-digital world, this is an episode full of clarity, conviction, and originality.

Time Stamps

03:12 – Why Bryony left Microsoft to explore the edge of sex and tech

07:30 – From commune living to global stages: Breaking the “good girl” mold

12:50 – Creating an industry brick by brick (and Airbnb’ing her place to fund it)

18:40 – Show your work: What creative momentum really looks like

25:10 – Launching Sex Tech School and building a global founder community

32:40 – Startup hacks: Overcoming censorship, banking blocks, and stigma

39:00 – Sex tech vs. adult: Rebranding the category and gaining legitimacy

43:12 – Deepfakes, AI porn, and the loneliness epidemic

51:00 – Dating the algorithm: AI companions and emotional outsourcing

59:40 – Future of sex, future of self: The coming shift in intimacy and identity

01:08:12 – Burnout at 26: What it reveals about modern culture

01:14:00 – From scale-at-all-costs to self-integration: Rethinking founder culture

01:16:30 – Through-topia, not utopia: What’s next for humans and tech

01:20:15 – The next podcast? Bryony names it on the spot

Resources

👩‍💻 Bryony Cole’s LinkedIn - https://www.linkedin.com/in/bryonycole/

🎙 Future of Sex - https://futureofsex.com/

🌐 Sex Tech School - https://www.sextechschool.com/

Sponsors:

Perspective X is supported by our wonderful sponsors:

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

Perspective X is part of Day One.

Day One helps founders and startup operators make better business decisions more often.

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

Mentioned in this episode:

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Eden Shirley, founder and CEO of AutoGuru, shares how he turned a near-collapse during COVID-19 into a high-growth B2B success story with FleetGuru. Eden breaks down how AutoGuru evolved from a consumer marketplace for car servicing into a powerful SaaS platform processing over 35,000 fleet transactions a month across Australia and New Zealand. He explains how strategic product pivots, a relentless focus on financial discipline, and embracing embedded payments technology unlocked new revenue streams and transformed the business model.

He reveals hard-won lessons on surviving financial crises, why raising startup capital before you need it is critical, and how founders can successfully scale by empowering their teams. This episode covers everything from navigating startup funding challenges and investor management to building a scalable B2B SaaS platform and leading through market uncertainty. If you’re exploring business model transformation, growth strategies for SaaS startups, or the leap from founder-led operations to sustainable leadership, this conversation is packed with actionable insights for long-term business resilience.

Time Stamps

02:04 – The adolescent startup mindset: Why AutoGuru still feels like day one

09:55 – COVID hits: Facing near collapse and the “Great Pivot”

17:07 – The real story behind raising capital during a crisis

23:35 – Bootstrapping vs. raising, why timing is everything

27:10 – Building a culture of warriors: How Eden kept his team together

35:00 – The B2B pivot: Launching FleetGuru and unlocking hypergrowth

42:33 – Processing $1M a day: Scaling B2B transactions and embedded payments

46:00 – Letting go of control: Transitioning from founder-led to scalable leadership

53:00 – Managing investor pressure and recapitalizing the business

59:10 – Health, burnout, and the personal cost of startup life

01:03:00 – Building a global-ready SaaS platform: The leap to New Zealand

01:10:00 – Growing from 50 to 100 employees: How Eden is planning for scale

01:18:11 – Why optimism is critical at the scale-up stage

01:22:41 – The key metrics every founder should track (and why revenue per employee matters)

01:29:00 – What’s next for Eden: The exit vision and building a global business

Resources

🚗 AutoGuru – Australia’s leading car servicing marketplace - https://www.autoguru.com.au/

👥 Connect with Eden Shirley on LinkedIn - https://www.linkedin.com/in/edenshirley

Sponsors:

Perspective X is supported by our wonderful sponsors:

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

Perspective X is part of Day One.

Day One helps founders and startup operators make better business decisions more often.

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

Mentioned in this episode:

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In Perspective X, host Pauline Fetaui dives deep into conversations with extraordinary entrepreneurs and leading innovators to explore not just their successes—but the overlooked decisions, mindset shifts, and personal turning points that sparked their greatest breakthroughs.

This show is about the ripple effect of choice: how deep accountability enables us to respond intentionally to life's challenges, rather than simply reacting. If you're curious about the inner journey behind meaningful achievements and how leaders evolve through adversity, this podcast is for you.

Join us on Perspective X, where we move beyond the highlight reel and into the pivotal moments that changed everything.

Launching on the 12th of May, wherever you get your podcasts.

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