Oversubscribed 💰

Are the best founders... damaged? 👀

That is the debate that lights up the Oversubscribed season finale, and it gets SPICY. Jessy Wu makes the case that VCs are quietly hunting for founders with a chip on their shoulder, and that investors have a low key incentive to keep them in that triggered, vindication-chasing state. Steve Baxter is not having it. What follows is one of the most honest conversations we've had on the show about ambition, ego, and what actually makes a founder great.

And that is just one part of a STACKED finale. HJ Jayakody tells the story of building Australia's secret space company, the one taking photos of satellites from other satellites at 15 kilometres a second. They set out to mine asteroids, accidentally snapped the International Space Station during COVID lockdown, got a call from US regulators, and ended up helping deregulate an entire industry.

Plus Steve's Shark Tank stories, because of course. Including how he landed the gig with two days notice while his brand new plane was literally on fire in the background.

Three guests, one room, zero filler. The perfect way to close out season one.

Brand new show this week for founders & operators grappling with the impact of AI on team building.

Yes I am SCREAMING in my room while typing this. In The Blink of AI is now the TOP 25 Business Podcasts in Australia on Spotify. BIGGEST thank you to everyone listening, sharing, and bingeing through the back catalogue.

I am screaming even louder while typing that we have been getting bigger guests for you every episode, and this month we have the Co-Founder of Notion, Chief Engineer of Generative AI at Commonwealth Bank, and the GM of ANZ at ElevenLabs.

The range is wild, and it makes for the perfect 3-4 hour morning run or commute. Queue them up.

Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders. It’s why more than 40,000 fast-growing companies trust Deel to move fast.

First Cheque 💵

Alexey Mitko built what is likely the biggest employee payout in Australian history. As Co-Founder of Eucalyptus, recently sold to Hims, and the architect of the ESOP plans at Canva and Koala, he designed the plan that sent around $300 million back to employees. He joins Cheryl and Maxine to break down the three questions every founder gets wrong about equity, why he personally sat down with the first two hundred hires to explain it, and why most Australians wrongly discount their equity to zero. His reframe that stuck with me: think of your career as a sequence of bets, and eventually one lands.

If the IPO window is closed, M&A is how most of your portfolio will exit. Alex Feldman, founder of M&A advisory Tiger and Bear, joins to explain how to actually buy and sell companies when the market is doing crazy things. He gets into the "SaaSpocalypse" rattling tech valuations, why timing beats everything in M&A, and why M&A is a muscle you have to work long before you need it. His advice on when to sell, and why selling shares is just selling shares, is essential listening for any founder staring down a tough raise.

Pear Tree helps Australian and New Zealand founders build high-performing offshore teams without the agency middleman.

Most offshore horror stories aren't a talent problem, they're the result of agencies that overcharge clients while underpaying staff. Pear Tree does it differently: a direct, transparent model where your team is paid fairly, fully compliant, and focused on your business, at a fraction of local salaries.

Day One community members get a free team audit plus 20% off your first hire. Learn more at dayone.fm/peartree.

Pick My Brain 🧠

Neel Bhattacharya is the founder of LeadTrackAI, a platform built to solve one of the most common and costly problems in sales: leads that go cold because nobody followed up fast enough. After more than a decade in product management across the energy sector, Neel built an AI voice agent that calls a new lead the moment they submit a form, speaks just like a real person, and qualifies them before handing them off to a human salesperson.

Neel started with solar and battery installers, an industry she knows intimately, and has since expanded into automotive. In this episode, Neel joins Alan to talk about the very real challenge of being a solo founder spread too thin, why documenting your own sales process is just as important as building the product, and how to decide whether to go deeper into one industry or wider into new ones.

Alan also shares a genuinely useful productivity framework and a tool recommendation that any solo founder drowning in admin will want to steal.

Ask a question, get advice from Alan, or give feedback - https://www.speakpipe.com/pickmybrain

Pick My Brain is supported by our wonderful sponsor Galah Cyber

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Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles.

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PerspectiveX 🌌

Yas Grigaliunas, days after her $4 million raise hit the bank, her marriage fell apart and she was locked out of the company she built with her own hands. Yas unpacks the nine months spent on the outside watching people who barely understood her business burn through a million dollars, the hostile takeover, and fighting her way back in as majority shareholder, all the way to the $20 million Amazon partnership that arrived ten days before liquidation. It is the fall that founders are made to take alone, the story that usually stays hidden, and how she survived it without ever once choosing to be the victim of it. She lost the company, but she did not lose herself.

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