Pick My Brain

About Pick My Brain

Hosted by Alan ‘the nice one’ Jones, Pick My Brain is a Day One® show. Day One is the podcast network dedicated to founders, operators, and investors. Follow Pick My Brain through Day One on LinkedIn Sign up to get your startup pitches and for opportunities to be featured on the show.

Publisher

Day One®

Category

business · education · news

Language

en

Explicit

No

First episode

8 Apr 2025

Latest episode

25 Aug 2026

Latest episodes

31 episodes in the feed.

1. 

   25 Aug 2026

   The Buzzword That's Killing Your Pitch: Billy Chan on Alfred Travel

   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 (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 (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/ (https://www.alfredtravel.io/) - Billy Chan on LinkedIn – https://au.linkedin.com/in/billy-chan-4527818b (https://au.linkedin.com/in/billy-chan-4527818b) - Ask Alan a Question – https://speakpipe.com/pickmybrain (https://speakpipe.com/pickmybrain) - More from Alan Jones – https://www.startupfoundercoach.com (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

2. 

   18 Aug 2026

   Why You Should Think Global From Day One: Ilana Elbaz on Deel

   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 (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

3. 

   11 Aug 2026

   How Do You Grow a Marketplace When Both Sides Are Slow? Ishan Dan on RegenX

   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 (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 (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/ (https://www.regenx.io/) - Ishan Dan on LinkedIn – https://au.linkedin.com/in/ishandan (https://au.linkedin.com/in/ishandan) - Ask Alan a Question – https://speakpipe.com/pickmybrain (https://speakpipe.com/pickmybrain) - More from Alan Jones – https://www.startupfoundercoach.com (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

Who has been a guest on Pick My Brain

Names identified in recent episode analyses. Showing up to five guests.

• Clement Baissat
• Allen Fan
• Cole Cornford
• Gaurav Rana
• Elena Tsalanidis

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

149,173

Score snapshot 15 Sept 2025

Spotify

5.0 / 5

3 ratings

Podcast Authority Score: 55 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

64

Social presence

0

YouTube

86

Engagement

32

Contact Pick My Brain

Guest appearances

Does not typically book guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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