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