Pick My Brain with Alan 'the nice one' Jones

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.

Pick My Brain with Alan 'the nice one' Jones is a business podcast hosted by Unknown Host, with 31 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts Pick My Brain with Alan 'the nice one' Jones, a business show with 31 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

• 

  Episode #30

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

  Aug 25, 202643 min

  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

  ListenShow Notes
• 

  Episode #29

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

  Aug 18, 202637 min

  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

  ListenShow Notes
• 

  Episode #28

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

  Aug 11, 202634 min

  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

  ListenShow Notes
• 

  Episode #27

  How Do You Sell Software to an Industry That Won't Change? Mitchell Baker on Claimstack

  Jul 28, 202623 min

  $320 billion flows through Australia's commercial construction industry every year — and far too much of it still moves on spreadsheets and re-keyed purchase orders. Mitchell Baker spent 12 years inside that machine as a contract administrator — on John Holland's $250M shopping-centre rebuild, and on Facebook's £150M London HQ with Kier — watching well-paid people burn their days copying data that already existed. So he built Claimstack, a workflow platform that follows the money from tender to final account across the whole contractor chain. In this special Melbourne edition of Pick My Brain, recorded at Cremorne Digital Hub, Alan Jones digs into the genuinely hard part: selling new software into an industry famous for resisting it, and coaching a solo, self-taught founder on when — and how — to stop wearing every hat. You'll also hear the vibe-coding origin story (DataButton, then Cursor, then Claude Code in VS Code), how Mitch is funding the dream by selling off possessions while his partner foots the bills, the milestone-based "startup leave" deal that kept the relationship healthy, and the 15% ESOP he carved out of his friends-and-family round to lure senior talent. Time Stamps 00:00 – Intro: $320B a year, still moving on spreadsheets 02:07 – What Claimstack does: one platform for the whole contractor chain 02:36 – The $320 billion inefficiency it targets 03:35 – 12 years in the trenches: John Holland and Facebook's London HQ 05:32 – Live in market: onboarding the first pilot customers 05:55 – Vibe-coding it solo: DataButton, Cursor, then Claude Code 06:45 – Why he didn't wait for a co-founder 07:43 – Funding the dream, and the deal with his partner 11:08 – Selling into an industry that resists new software 14:26 – Building a sales team without losing credibility 15:37 – Marketing yourself with a LinkedIn feature series 17:48 – A solo founder's leadership gaps, and the 15% ESOP 19:26 – Wrap-up Resources Claimstack – https://claimstack.com.au Ask Alan a Question – https://speakpipe.com/pickmybrain More from Alan Jones – https://www.startupfoundercoach.com 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 $320 billion a year flows through Australian commercial construction, and much of it still moves on spreadsheets and re-keyed data. Mitchell Baker spent 12 years as a contract administrator — including on Facebook's London HQ — before building Claimstack to follow the money from tender to final account across the whole contractor chain. In this Melbourne edition of Pick My Brain, Alan Jones coaches Mitch on selling software into an industry that resists change, and on when a solo, self-taught founder should start building a team. Time Stamps 00:00 – Intro: $320B a year, still moving on spreadsheets 02:07 – What Claimstack does: one platform for the whole contractor chain 02:36 – The $320 billion inefficiency it targets 03:35 – 12 years in the trenches: John Holland and Facebook's London HQ 05:32 – Live in market: onboarding the first pilot customers 05:55 – Vibe-coding it solo: DataButton, Cursor, then Claude Code 06:45 – Why he didn't wait for a co-founder 07:43 – Funding the dream, and the deal with his partner 11:08 – Selling into an industry that resists new software 14:26 – Building a sales team without losing credibility 15:37 – Marketing yourself with a LinkedIn feature series 17:48 – A solo founder's leadership gaps, and the 15% ESOP 19:26 – Wrap-up Resources Claimstack – https://claimstack.com.au Ask Alan a Question – https://speakpipe.com/pickmybrain More from Alan Jones – https://www.startupfoundercoach.com Mentioned in this episode: Deel x PX_Script 1 Deel x PX_Script 2 Deel x PX_Script 1

  ListenShow Notes
• 

  Episode #26

  What's Your Moat When AI Can Copy Your Product in 48 Hours? | Dilip Jacob from Pitchberry

  Jul 7, 202629 minS1

  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 Sponsors: Pick My Brain is supported by our wonderful sponsors: 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 The Day One Network Pick My Brain is part of Day One, the podcast network dedicated to founders, operators & investors. 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

  ListenShow Notes

Recent guests on Pick My Brain with Alan 'the nice one' Jones. Study who booked and why before you pitch.

Based on semantic analysis of episode topics and host coverage, this show is a strong guest fit for executives in:

Industry fit is computed by PitchCentric using vector embeddings of the show's episode catalog.