『Pick My Brain with Alan 'the nice one' Jones』のカバーアート

Pick My Brain with Alan 'the nice one' Jones

Pick My Brain with Alan 'the nice one' Jones

著者： Day One®
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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.Day One® is a registered trademark of W2D1 Media Pty Ltd. マネジメント・リーダーシップ リーダーシップ 個人的成功 政治・政府 経済学 自己啓発
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  • How Do You Sell Software to an Industry That Won't Change? Mitchell Baker on Claimstack

    How Do You Sell Software to an Industry That Won't Change? Mitchell Baker on Claimstack
    2026/07/28
    $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 Stamps00:00 – Intro: $320B a year, still moving on spreadsheets02:07 – What Claimstack does: one platform for the whole contractor chain02:36 – The $320 billion inefficiency it targets03:35 – 12 years in the trenches: John Holland and Facebook's London HQ05:32 – Live in market: onboarding the first pilot customers05:55 – Vibe-coding it solo: DataButton, Cursor, then Claude Code06:45 – Why he didn't wait for a co-founder07:43 – Funding the dream, and the deal with his partner11:08 – Selling into an industry that resists new software14:26 – Building a sales team without losing credibility15:37 – Marketing yourself with a LinkedIn feature series17:48 – A solo founder's leadership gaps, and the 15% ESOP19:26 – Wrap-upResources🔗 Claimstack – https://claimstack.com.au🎙 Ask Alan a Question – https://speakpipe.com/pickmybrain🎧 More from Alan Jones – https://www.startupfoundercoach.comFounders 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/dayoneEpisode 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 Stamps00:00 – Intro: $320B a year, still moving on spreadsheets02:07 – What Claimstack does: one platform for the whole contractor chain02:36 – The $320 billion inefficiency it targets03:35 – 12 years in the trenches: John Holland and Facebook's London HQ05:32 – Live in market: onboarding the first pilot customers05:55 – Vibe-coding it solo: DataButton, Cursor, then Claude Code06:45 – Why he didn't wait for a co-founder07:43 – Funding the dream, and the deal with his partner11:08 – Selling into an industry that resists new software14:26 – Building a sales team without losing credibility15:37 – Marketing yourself with a LinkedIn feature series17:48 – A solo founder's leadership gaps, and the 15% ESOP19:26 – Wrap-upResources🔗 Claimstack – https://claimstack.com.au🎙 Ask Alan a Question – https://speakpipe.com/pickmybrain🎧 More from Alan Jones – https://www.startupfoundercoach.comMentioned in this episode:Deel x PX_Script 1Deel x PX_Script 2Deel x PX_Script 1
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    23 分
  • What's Your Moat When AI Can Copy Your Product in 48 Hours? | Dilip Jacob from Pitchberry

    What's Your Moat When AI Can Copy Your Product in 48 Hours? | Dilip Jacob from Pitchberry
    2026/07/07

    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 NetworkPick 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
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    29 分
  • The Four-Quadrant Framework Every Solo Founder Needs | Neel Bhattacharya from LeadTrackAI

    The Four-Quadrant Framework Every Solo Founder Needs | Neel Bhattacharya from LeadTrackAI
    2026/06/24

    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

    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 NetworkPick 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:

    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.
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    27 分
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