Pick My Brain is supported by our wonderful sponsors:

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

Episode Summary

Travellers can spend 15 hours over two months planning a holiday, then arrive with a messy spreadsheet, a graveyard of email confirmations and a screen full of Google Maps pins. Billy Chan and his co-founder built Alfred Travel to turn that fragmented process into a personalised, mobile itinerary travellers can edit, validate and book.

Alfred Travel had passed 1,300 users when Billy joined Pick My Brain. The company had closed a $250,000 pre-seed round and was preparing to raise $500,000 at a $5 million cap after reaching 15,000 users. Alan Jones puts on his investor hat to stress-test the story — and immediately finds the buzzword getting in its way.

They explore why “AI-powered” no longer earns points in a pitch, how Billy can teach investors something they do not already know about travel, and why a low-margin travel business has to think globally from day one. They also tackle geopolitical uncertainty, capital planning, affiliate economics and why Alfred's proposed loyalty token belongs in horizon two, after the company has built meaningful scale.

Time Stamps

00:00 – The buzzwords investors are tired of hearing

00:59 – Welcome to Pick My Brain

01:51 – Meet Billy Chan and Alfred Travel

02:18 – From curious kid to technology founder

03:49 – The 15-hour holiday-planning problem

05:13 – How Alfred Travel makes money

05:40 – The founding team and a ten-year-old idea

07:01 – Why Alfred is a native mobile app

08:08 – Early traction and the ideal customer

09:24 – Personalisation without hallucinations

12:51 – Closing the booking loop

14:12 – The affiliate revenue problem

15:20 – The $500,000 seed-round plan

16:37 – Why “AI-powered” weakens the pitch

23:06 – Addressing global travel uncertainty

27:18 – Building a global company from day one

28:58 – Teach investors something they do not know

32:32 – Why this business cannot be cautious about growth

34:13 – Escaping the Australian launchpad mindset

36:57 – Loyalty tokens and the horizon-two trap

40:12 – Wrap-up

Resources

- Alfred Travel – https://www.alfredtravel.io/

- Billy Chan on LinkedIn – https://au.linkedin.com/in/billy-chan-4527818b

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

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

About Pick My Brain

Pick My Brain is a Day One show hosted by startup founder coach and investor Alan Jones.

Mentioned in this episode:

Deel x PX_Script 1

Deel x PX_Script 2

Pick My Brain is supported by our wonderful sponsors:

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

Episode Summary

Ilana Elbaz joined Deel when it was five people, one developer and no revenue. It is now 7,200 people across almost every timezone, with more than $1 billion in ARR — and it has never had an office. She built the go-to-market function that got it there, from Singapore, having grown up in France and started companies in Thailand, Switzerland and the US.

Deel went through Y Combinator in 2019 as something else entirely — first a social media product, then a blockchain company — before landing on the payroll, compliance and employment infrastructure it sells today. Much of that product exists because Deel needed it first: the employer-of-record product was built after contractors in Germany and Italy told the company they would not work as contractors.

In this episode of Pick My Brain, Alan Jones asks the question every Australian founder eventually hits: if the local market is small and the experienced talent is thin, when do you start hiring offshore? Ilana's answer is blunter than most — think global from day one, for the team and for the go-to-market, because the alternative is optimising for proximity instead of quality.

They also get into the compliance mistakes that can close a business, why an investor will interrogate your workforce structure at the next round, how Deel runs on written async communication and huddles instead of scheduled one-on-ones, and Ilana's case that the classic weekly one-on-one is obsolete once you have real-time data. Plus the SDRs who went from under $40,000 a year to more than $500,000, and why she would take that job again tomorrow.

Time Stamps

• 00:00 – Five people to 7,200, and zero to over a billion
• 00:58 – Welcome to Pick My Brain
• 01:45 – Meet Ilana Elbaz, head of sales and go-to-market at Deel
• 02:30 – Doctor or entrepreneur, and a first company at 19
• 05:02 – How Deel was founded, and the pivots through Y Combinator
• 07:26 – Is Y Combinator still worth applying for?
• 08:50 – Remote-first from day one, and why proximity is a bad filter
• 10:56 – Eating your own dog food: how the employer-of-record product got built
• 12:29 – Where 7,200 people actually sit
• 14:34 – Why a small market forces Australian founders outward
• 16:41 – Slack from day one: async, written and measured
• 18:07 – Akai by Deel and the daily performance report
• 19:58 – Think global from day one
• 21:08 – The compliance mistakes that can close your business
• 22:59 – Paying people in the currency they actually want
• 25:56 – Onboarding, buddies and enablement
• 26:33 – From under $40k to over $500k: the SDR path
• 27:56 – Bringing a distributed team together, and the Deel World Cup
• 30:24 – Why the classic one-on-one is obsolete
• 32:43 – Fix it now: the cost of postponing hard conversations
• 33:30 – Wrap-up

Resources

- Deel – https://www.deel.com/dayone

- Ilana Elbaz on LinkedIn – https://www.linkedin.com/in/ilanaelbaz

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

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

Pick My Brain is a Day One show hosted by startup founder coach and investor Alan Jones.

Mentioned in this episode:

Deel x PX_Script 1

Deel x PX_Script 2

Pick My Brain is supported by our wonderful sponsors:

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

Episode Summary

Alternative investments can give investors exposure beyond shares and bonds, but most clean-energy projects still come with high minimums, expensive structuring and long, relationship-driven sales cycles. Ishan Dan founded RegenX to help developers make those projects investment-ready and give wholesale investors access at a more practical scale.

In this episode of Pick My Brain, Alan Jones helps Ishan confront the hardest part of the model: RegenX is a two-sided marketplace, and neither side moves quickly. Project developers need capital, while wealth managers and family offices need trust, evidence and a reason to pay attention.

They unpack how to stop treating both sides as equal growth problems, why one-to-many relationship building can outperform another round of cold outreach, and how a founder becomes the credible industry expert the market needs. Ishan also shares RegenX's fee model, early project pipeline and the regulatory constraints behind raising capital for clean-energy assets.

Time Stamps

00:00 – Why RegenX is changing access to alternative investments

01:25 – Welcome to Pick My Brain

02:14 – Ishan's question for Alan

02:54 – From aspiring stockbroker to startup founder

04:40 – What counts as an alternative investment?

05:33 – Making clean-energy projects investment-ready

11:36 – RegenX's first projects and $60 million pipeline

13:13 – The hardest part of raising capital

17:43 – Why two-sided marketplaces are so difficult

24:25 – Trust, relationships and wealth managers

29:06 – Becoming the industry expert

29:43 – Making one side someone else's growth problem

31:34 – Wrap-up

Resources

- RegenX – https://www.regenx.io/

- Ishan Dan on LinkedIn – https://au.linkedin.com/in/ishandan

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

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

Pick My Brain is a Day One show hosted by startup founder coach and investor Alan Jones.

Mentioned in this episode:

Deel x PX_Script 2

Deel x PX_Script 1

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: Global hiring and payroll can be a headache. Deel brings HR, IT and payroll together in one platform, helping companies including Shopify, Revolut and ElevenLabs scale internationally.

Ready to expand your business?

Build your global team with Deel at 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: Global hiring and payroll can be a headache. Deel brings HR, IT and payroll together in one platform, helping companies including Shopify, Revolut and ElevenLabs scale internationally.

Ready to expand your business?

Build your global team with Deel at 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: Global hiring and payroll can be a headache. Deel brings HR, IT and payroll together in one platform, helping companies including Shopify, Revolut and ElevenLabs scale internationally.

Ready to expand your business?

Build your global team with Deel at 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: Global hiring and payroll can be a headache. Deel brings HR, IT and payroll together in one platform, helping companies including Shopify, Revolut and ElevenLabs scale internationally.

Ready to expand your business?

Build your global team with Deel at 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.