Dilip Jacob is the solo founder and CEO of Pitchberry, an AI platform that helps people in high-stakes professions practice the conversations their careers depend on. The idea came from a very personal place: diagnosed with high anxiety, Dilip froze during an investment pitch and went looking for a way to get better. What began as a tool for founders found an unexpected first market in dentistry, where internationally trained dentists must pass a communication-heavy exam to work in Australia. Pitchberry now has 300+ users.

This episode is a masterclass in the decisions every early-stage founder faces. Dilip and Alan work through how to find a co-founder without rushing into the wrong partnership, why the language you use changes how convincing you sound, and whether to raise capital or bootstrap when you already have paying customers in sight. Alan also breaks down the four things every founder needs before they're investible, including the one most solo founders never fix.

Stick around for the last section, where Alan tackles the question keeping most AI founders up at night: what counts as a defensible moat when anyone can rebuild your product in 48 hours? His answer, user context and brand relationship, might change how you think about your entire product strategy.

Timestamps

02:30 – How Pitchberry was born from Dilip's own struggle with pitch anxiety

04:00 – The professions that rely on credibility: doctors, dentists, lawyers, police and founders

05:30 – Why dentistry became Pitchberry's unexpected first market

06:15 – The go-to-market model: free practices, paid subscriptions and token costs

07:30 – Pivoting from individual users to selling into institutions and academies

09:00 – The challenges of being a solo founder and reaching out for a co-founder

10:00 – How small language changes make you sound more convincing to any audience

11:30 – Why a co-founder relationship is harder than a marriage, and how to date first

13:30 – Where to find co-founders: YC's co-founder matching and networking events

15:00 – Should you raise funding or bootstrap? The case for staying in control

18:00 – Why bootstrapped Aussie success stories like Atlassian and Campaign Monitor matter

20:00 – The four things every founder needs to be investible

22:00 – What counts as a defensible moat now that AI can replicate any product

25:00 – Why user context and brand relationship are the real moats in the age of AI

Deel: 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.

Visit https://www.deel.com/dayone

___

Galah Cyber offers Application Security Assessment Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at https://www.galahcyber.com.au/assess

To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

Mentioned in this episode:

5 I’s of Application Security Assessment

Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at galahcyber.com.au/assess.

Deel x PX_Script 2

Deel x PX_Script 1

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.

Timestamps:

01:27 – Neel's origin story: from wanting to be an architect to a decade in energy product management

03:01 – Why Neel left corporate to become a founder

03:44 – Who LeadTrackAI is for and the problem it solves for solar and battery resellers

05:06 – How the AI voice agent works: calling leads the moment they come in

06:32 – Why a fresh, qualified lead is worth more than ten cold ones

07:01 – Where LeadTrackAI is today: three large customers and expanding to Sydney

08:55 – Why every call is transcribed and how that builds an audit trail for regulated industries

09:57 – The founder's trap: chasing shiny objects instead of documenting what works

11:27 – Alan's four-quadrant framework for prioritising urgent vs important tasks

14:28 – Why SOPs and financial admin always end up in the "important but not urgent" pile

16:01 – Using AI to observe your own work as a founder, not just to build product

17:39 – Neel's big question: go deeper into solar and automotive, or go wider into new industries

18:17 – Alan's advice: run a cheap landing page experiment before committing to a new vertical

22:31 – Why charitable and nonprofit donation pipelines could be the next great use case for LeadTrackAI

Deel: 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.

Visit https://www.deel.com/dayone

___

Galah Cyber offers Application Security Assessment Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at https://www.galahcyber.com.au/assess

To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

Mentioned in this episode:

Deel x PX_Script 2

Deel x PX_Script 1

5 I’s of Application Security Assessment

Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at galahcyber.com.au/assess.

Most people think private messaging is already solved. Chris Fresle is proof it isn't.

Chris Fresle is the founder of Just Us, a private messaging app built to prevent image-based abuse. He's a year nine dropout with no tech background, a patent pending across six countries, and a product that uses facial recognition and object detection to make private messages genuinely impossible to screenshot, forward, or capture on another device.

In this episode, Chris joins Alan at the Cremorne Digital Hub in Melbourne to talk through how he built something everyone said was impossible, how he found and trusted a development team in Vietnam with no technical knowledge of his own, and how he's using survivor-led influencer marketing to build trust with a Gen Z audience that WhatsApp and Signal have never been able to reach.

Stay until the end for Chris's take on why Australian investors are harder to crack than US investors, and Alan's advice on how to pitch a product that people struggle to believe actually works.

Timestamps

00:00 Intro

03:00 The Journey to Creating Just Us

06:02 Building a Trustworthy Team

08:55 Navigating Skepticism in the Startup World

12:00 Monetization and User Engagement Strategies

15:07 User Feedback and App Development

17:58 Marketing and Influencer Partnerships

20:50 Protecting Intellectual Property

23:56 The Vision for Just Us

27:14 Passion for Change and Helping Others

Deel: 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.

Visit https://www.deel.com/dayone

___

Galah Cyber offers Application Security Assessment Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at https://www.galahcyber.com.au/assess

To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

Mentioned in this episode:

5 I’s of Application Security Assessment

Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at galahcyber.com.au/assess.

Deel x PX_Script 1

Deel x PX_Script 2

Quinnie Chen is the founder of Profit Plainly, a web app built for solo founders and freelancers who have no finance team, no CFO, and no clear picture of whether their business is actually working for them. Quinnie built it to solve her own problem, after years of running a website and software design business post Canva, she kept reaching the end of the month and realising she had underpriced her work, taken on the wrong clients, and had no way of knowing what she actually needed to earn to replace a salary.

In this episode, recorded live at the Cremorne Digital Hub in Melbourne, Quinnie joins Alan to talk through the early stages of bringing Profit Plainly to market. Alan challenges her to think more carefully about who her first customer really is, why accountants and bookkeepers might be her smartest go-to-market channel, and why per-usage pricing could unlock growth that a traditional SaaS model would block. It's a candid, practical conversation about the decisions every solo founder faces before they have any customers, any pricing, and any real clarity on where to focus.

If you're building something early and trying to figure out where to start, this episode is for you.

Time Stamps

00:00 Trailer and Intro

03:01 How Quinnie Chen Built Profit Plainly to Solve Her Own Freelancing Finance Problem

05:47 Why Emotional Labor and Opportunity Cost Are Missing From Most Business Finance Tools

08:52 How the Business Ikigai Framework Helps Solo Founders Identify Their Best Clients

12:05 Why Accountants and Bookkeepers Are the Smartest First Customer for Profit Plainly

14:54 How to Find a Go-To-Market Channel That Generates Both Revenue and Referrals

18:02 Why Traditional SaaS Pricing May Not Work for Price-Sensitive Solo Founders

21:04 How Per-Usage Pricing Could Help Profit Plainly Convert More Early Stage Users

23:46 How to Start Experimenting With Paid Marketing Before Your Product Is Ready

27:14 How to Build a Community and Reward Engaged Users on a Zero Budget

30:03 How to Join the Profit Plainly Early Access Beta and What Comes Next

Deel: 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.

Visit https://www.deel.com/dayone

___

Galah Cyber offers Application Security Assessment Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at https://www.galahcyber.com.au/assess

To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

Mentioned in this episode:

Deel x PX_Script 1

Deel x PX_Script 2

5 I’s of Application Security Assessment

Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at galahcyber.com.au/assess.

Tap, beep, done. Australia’s payment experience is one of the world’s most convenient, but also one of the most expensive. Small businesses lose thousands a month in card and scheme fees, while everyday Australians pay hundreds each year just to access their own money.

In this episode of Pick My Brain, Gaurav Rana, co-founder of GANI Pay, joins Alan Jones to pitch his mobile-first payment platform designed to bypass the legacy card system entirely. GANI Pay uses NPP, PayID, and PayTo to enable instant, secure QR payments, with flat monthly fees for merchants and cash-back rewards for consumers.

Alan and Gaurav dig into the economics of “tap and go,” how to convince both merchants and customers to switch, and why regulatory trust is just as important as slick tech in fintech. They also explore GANI Pay’s go-to-market focus on high-volume, low-ticket retailers, and what it takes to turn a payment product into a movement.

If you’re building in fintech, payments, or tackling an entrenched incumbent, this is a masterclass in pitching, positioning, and finding your wedge.

Time Stamp

01:40 – What is GaniPay? Mobile-first QR payments without the card fees

03:00 – Gaurav’s early ambitions: from science to entrepreneurship

04:15 – The problem: why tap payments quietly cost Australians billions

06:10 – How GaniPay works: bypassing Visa/Mastercard with NPP & PayTo

08:20 – Merchants’ biggest question: will customers adopt it?

09:50 – Building trust: compliance, security, and banking partnerships

12:15 – Go-to-market: targeting high-volume, sub-$100 transactions

14:30 – Competing with Afterpay & co: different problem, different value

15:55 – Alan on finding the most promising merchant verticals

17:40 – Fundraising plans: seeking $600k to scale tech & marketing

18:35 – How to become an “investable” fintech in 60 days

20:45 – Movement vs product: can GaniPay spark a payments revolution?

Resources

🙋🏻‍♂️ Gaurav Rana – https://www.linkedin.com/in/gauravrana841/

💰 GaniPay – https://ganipay.com.au/

Deel: 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.

Visit https://www.deel.com/dayone

___

Galah Cyber offers Application Security Assessment Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at https://www.galahcyber.com.au/assess

To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

Mentioned in this episode:

Deel x PX_Script 1

Deel x PX_Script 2

Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey

Justin Wastnage is the founder and CEO of Vloggi, a platform that transforms everyday mobile phone footage into trusted, structured, legally owned video assets for businesses and enterprises. What started as a tool for tourism boards to crowdsource location content has evolved, through COVID, multiple pivots, and years of customer-funded development, into an infrastructure layer that verifies, structures and processes video for some of the world's most compliance-heavy industries.

In this episode, Justin joins Alan to talk honestly about the challenges of pitching a business that investors think they already know. Vloggi has worked with Major League Baseball, Netflix, the NSW Government, Google Ads and RFK's presidential campaign, yet raising in Australia remains stubbornly difficult. Alan digs into why that is and what Justin can do about it, from repositioning the pitch, to rebranding, to putting someone else in the room.

If you're a founder who has pivoted hard but can't shake what investors remember about your old story, this one is for you.

00:00 - Intro

02:03 – Meet Justin Wastnage and the origins of Vloggi

04:57 – What Vloggi does: video as content, data and evidence

07:11 – What changed with synthetic AI video and why it matters now

09:00 – The pivot story: from tourism boards to enterprise compliance

12:35 – Bootstrapping and the team behind Vloggi

13:03 – The current raise: $800k to bring the enterprise product to market

17:03 – How Vloggi verifies that uploaded video is authentic, not AI-generated

19:33 – Commercial model: per project vs ongoing enterprise licensing

22:31 – Why Vloggi wants to be infrastructure, not a consumer brand

24:48 – Alan's challenge: how to reposition when investors think they know your old story

29:08 – Should you rebrand? The case for and against

32:26 – Pitch deck strategy: teaser first or full deck upfront?

35:23 – Alan pitches Vloggi back to Justin the way he'd do it

38:51 – The airline use case and how to open with one vertical then go broad

Deel: 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.

Visit https://www.deel.com/dayone

___

Galah Cyber offers Application Security Assessment Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at https://www.galahcyber.com.au/assess

Deel: 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.

Visit https://www.deel.com/dayone

___

Galah Cyber offers Application Security Assessment Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at https://www.galahcyber.com.au/assess

Mentioned in this episode:

Deel x PX_Script 2

Deel x PX_Script 1

Win $2,000 in credits with the Day One Network — take our 2-minute audience survey before 30 June: dayone.fm/survey

In this episode, Ben joins Alan to talk about what it actually looks like to build and scale a technical consulting business in Australia, from the talent shortage that forces most serious engineering firms offshore, to the practical realities of using AI in production versus just prototyping. Ben is refreshingly direct about what works and what doesn't, including why he thinks signing a three-year deal with any AI provider right now is a mistake, why AI cold email campaigns do more damage than good, and why a physical piece of mail will outperform ten thousand automated messages every time.

Alan challenges Ben on the right tech stack for founders heading into 2026, how to get the most out of free cloud credits before you raise, and what product managers still do better than any AI tool on the market.

If you're a founder making decisions about how to build, who to hire, or which AI tools to trust with your business, this episode is worth your time.

🎙 Ask Alan a Question – https://speakpipe.com/pickmybrain

🎧 More from Alan Jones – https://www.startupfoundercoach.com

Deel: 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.

Visit https://www.deel.com/dayone

___

Galah Cyber offers Application Security Assessment Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at https://www.galahcyber.com.au/assess

To learn more, join our newsletter to be notified of new and upcoming shows. The only content we create is content that will help Australian founders.

Mentioned in this episode:

Deel x PX_Script 1