Skip to content
Sign inOpen the app
Artwork for The Startup Playbook Podcast
Business

The Startup Playbook Podcast

Rohit Bhargava - Entrepreneur | Blogger | Podcaster. I help launch, grow and fund startups and online businesses

Every week, I interview successful entrepreneurs, investors and business industry experts on how they got started, the strategies they used to succeed and their advice to current and future entrepreneurs

SubscribePlay latestOpen in podnodRSS feedShow website
  • 20 episodes
  • Updated Sep 25, 2025

Episodes20

Newest first
  • Sep 25, 2025 · 1 hr 7 min

    Ep220 – Adam Ewart (Co-founder & CEO – Send My Bag) on bootstrapping Send My Bag from a uni side project to global service

    My guest for Ep220 of The Startup Playbook Podcast was Adam Ewart, the Co-founder & CEO of Send My Bag. Send My Bag is the international luggage shipping and relocation platform used by travellers and businesses around the world. Adam’s story is a fascinating one. From building a global company out of a small town in Northern Ireland, to turning PR into a powerful growth engine, to deliberately bootstrapping even when VCs came knocking, his journey is full of practical lessons and hard-earned insights. In this episode we dive into: How he turned PR into one of his biggest growth drivers Why he chose to bootstrap despite inbound investor interest The challenges and opportunities of building a large global business out of Belfast Timestamps: 00:02:15 Adam’s early entrepreneurial roots and family business influences 00:07:00 Why Adam never wanted a traditional job 00:08:10 Using part-time wages and student loan to fund ventures 00:10:45 First experiments: Middleman Mobiles and FillAJob.com 00:13:30 The idea for Send My Bag 00:18:20 First customers: student shipping during summer holidays 00:27:00 From domestic student shipping to international expansion 00:29:00 Spotting the airline baggage fee opportunity and PR growth 00:34:00 Leveraging free publicity: Dragons’ Den appearance 00:40:15 Expanding into the U.S. market and securing media coverage 00:45:30 Building Send My Bag into a relocation and global logistics service 00:52:00 Lessons learned on scaling, growth and resilience Our partners: A big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club: The world’s first human accelerator Adam’s links: Send My Bag Adam on Twitter/X People mentioned: Grant Carmichael Companies mentioned: FillAJob.com (no longer active) Dragons’ Den (BBC) American Airlines Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep220 – Adam Ewart (Co-founder & CEO – Send My Bag) on bootstrapping Send My Bag from a uni side project to global service appeared first on Startup Playbook.

  • Aug 28, 2025 · 1 hr 6 min

    Ep219 – Stirling Mortlock (Co-founder – XV Capital) on the journey from Wallabies Captain to Sports-Tech Investor

    The Startup Playbook Podcast Insights and lessons from the world's best entrepreneurs and investors Twitter Facebook YouTube Instagram Ep219 – Stirling Mortlock (Co-founder – XV Capital) on the journey from Wallabies Captain to Sports-Tech Investor August 28, 2025 rohitbhargava Podcast My guest for Ep219 of The Startup Playbook Podcast was Stirling Mortlock. Stirling is one of Australia’s greatest ever Rugby players. He’s a former Wallabies Captain, World Cup player, and one of the few players to score over 1,000 points in Super Rugby. But his story goes well beyond the field. After retiring, he’s built a career as a founder and investor. Today, he’s the Co-founder of XV Capital, where he’s backing the next generation of sports-tech and performance-led startups. In this episode we dive into: Lessons from professional rugby and how he’s applied them to his career post sport The rhythms & role clarity behind high-performance teams A resilience playbook: “feed the good wolf” through injuries & setbacks Where sports-tech is heading And much more! I’m also excited to announce that Stirling will be joining The Komo Club as a speaker for Cohort 2. The program is the world’s first human accelerator, designed to help high performing founders and executives implement the right system and frameworks to help them succeed in business and all areas of their life. You can find out more at thekomoclub.com Timestamps: 00:02:15 Career arc: Brumbies mainstay, two World Cups, captaincy at Brumbies/Wallabies/Rebels, transition to life after rugby. 00:07:08 Obsession with sport, MJ as childhood idol, and setting audacious goals back in Year 11. 00:09:31 Overlooked early, late physical growth, and training like a pro at uni: why hard work fast-tracked selection. 00:12:07 “Outliers” & relative age: flipping a potential disadvantage into a slingshot advantage. 00:15:00 Seizing rep opportunities: NSW Country vs City, shadow call-up 00:18:44 Keeping belief amid uncertainty: mentors and the power of goal-setting. 00:27:26 Inside high-performance teams: weekly rhythm, role clarity, and leveraging strengths under pressure. 00:30:24 Captaincy lessons: delegate to strengths and always do your job lead by example. 00:32:28 Turning ADHD into a superpower; creating environments where people operate at their “optimal frequency.” 00:48:37 Future of Sports-Tech 00:59:38 15 operations & the “feed the good wolf” framework for setbacks; silver linings during rehab. Our partners: A big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club: The world’s first human accelerator Stirling’s links: Stirling on LinkedIn XV Capital People mentioned: James Godfrey Gordon Ogilvy Mark Davis Phil Waugh Jeremy Mortlock Chris Malone Andrew Walker Tim Horan Jason Little George Gregan Stephen Larkham Joe Roff Chuck Carter Mel Brown Companies & Organisations mentioned: Prevent Biometrics ACT Brumbies Melbourne Rebels Wallabies (Rugby Australia) Gordon Rugby Club Rugby Australia Australian Institute of Sport (AIS) British & Irish Lions Resources mentioned: Outliers by Malcolm Gladwell Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here admin January 1, 2014 Reply Lorem ipsum dolor sit amet, consectetur adipisicing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat admin January 1, 2014 Reply Lorem ipsum dolor sit amet, consectetur adipisicing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat admin January 1, 2014 Reply Lorem ipsum dolor sit amet, consectetur adipisicing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. Copyright © 2015 - Live Composer The post Ep219 – Stirling Mortlock (Co-founder – XV Capital) on the journey from Wallabies Captain to Sports-Tech Investor appeared first on Startup Playbook.

  • Aug 7, 2025 · 1 hr 7 min

    Ep218 – Nipun Mehra (Co-founder & CEO – Ula) On Ula’s hypergrowth, Bezos backing & the hard call to shut down

    My guest for Ep218 of The Startup Playbook Podcast was Nipun Mehra. Nipun has had an incredible track record in his career. At Amazon he launched their first ever real time inventory management system, was an early team member at Flipkart helping build and scale one of India’s most successful and iconic startups before joining Sequoia India as an investor. In 2020, he Co-founded Ula, a B2B e-commerce platform that set out to modernise retail supply chains for millions of small businesses starting in Indonesia. Ula quickly become one of South East Asia’s fastest growing startups. They went from $0 to $300M in revenue within 2 years. Ola also raised over $140M from leading investors including Sequoia, Lightspeed, Tencent and even raised capital from Jeff Bezos himself, his first investment into this part of the world. But in a candid and deeply honest conversation, Nipun shares – for the first time publicly – the full story of what happened behind the scenes from Ula when he decided to shut down the company and return the remaining capital to investors. From hypergrowth to hard calls, this episode dives into the reality of building a company at scale and the weight of leadership at challenging times. In this episode we cover: Nipun’s lessons from his time with Amazon, Flipkart and Sequoia The hypergrowth journey behind Ula Why he decided to shut down Ula and return the capital vs find another path Coming to terms with the ups and downs of the journey & much more I’m also excited to announce that Nipun will be joining The Komo Club as a speaker for Cohort 2. The program is the world’s first human accelerator, designed to help high performing founders and executives implement the right system and frameworks to help them succeed in business and all areas of their life. You can find out more at thekomoclub.com Timestamps: 00:03:08 Nipun’s background: Early entrepreneurial drive 00:07:00 College startup attempts and discovering India’s nascent internet scene 00:14:47 What Amazon & Flipkart taught him about audacious targets and culture 00:20:38 How to set “aggressive but achievable” goals without crossing into folly 00:29:23 Why Indonesia? The leap of faith that launched Ula in Southeast Asia 00:38:37 Securing Jeff Bezos’ first SEA investment and the six-page memo that closed the deal 00:41:31 Scaling to ~US $300 M GMV in two years during COVID 00:43:20 The decision to shut down Ula and return the remaining capital to investors 00:55:13 Lessons on investor alignment 01:04:45 Nipun’s new venture, lessons from Ula he’s applying Our partners: Thank you to Karl Noronha, Ganesh Rengaswamy and Prithvi Rajaram for their help with research for this interview! A big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club: The world’s first human accelerator Nipun’s links: Nipun on LinkedIn People mentioned: Jeff Bezos Larry Page Marissa Mayer Elon Musk Karl Noronha Ganesh Rengaswamy Prithvi Rajaram Companies mentioned: Ula Amazon Flipkart PhonePe Sequoia Capital India / Peak XV Partners Lightspeed Venture Partners Boston Consulting Group Tiger Global Tencent Prosus Bezos Expeditions Udaan Shopee Mercado Libre Coupang Google Meta Reliance Jio Reliance Industries Gojek Tokopedia Playbook Ventures Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep218 – Nipun Mehra (Co-founder & CEO – Ula) On Ula’s hypergrowth, Bezos backing & the hard call to shut down appeared first on Startup Playbook.

  • Jul 24, 2025 · 1 hr 39 min

    Ep217 – Dr Steven Lu (Co-founder & CMO – Everlab) on building the future of preventative health

    My guest for Ep217 of The Startup Playbook Podcast was Dr. Steven Lu. Dr. Steven Lu is the Co-founder and Chief Medical Officer of Everlab, Australia’s leading preventative health and longevity startups. With over 15 years of clinical experience, Steven specialised in the prevention and management of complex medical conditions including heart attacks and strokes. After years of treating late-stage illness, he shifted focus to building a proactive model of healthcare, one that empowers people to catch risks early and take control of their long-term health. That idea became Everlab. Since launching, Everlab has scaled rapidly across Australia, combining full-body diagnostics, personalised blood testing, and AI-driven insights to make preventative healthcare more accessible and actionable. The company recently closed a $15M AUD Seed round led by New York based Left Lane Capital. I was proud to continue backing Steven and the Everlab team through Playbook Ventures in this latest round. In addition to our investment, I’ve had the pleasure of working with Steven through The Komo Club, where he’s a featured speaker in both Cohort 1 and 2. The Komo Club has also partnered with Everlab who support our members directly with DEXA scans, blood testing, and 1:1 medical consultations as part of their cohort experience. In this episode, we discuss: Steven’s transition from private practice to founding Everlab The shortcomings of traditional healthcare and Everlab’s approach to solving them The key health pillars every founder should build into their routine How Steven manages his own health and family life while scaling a startup Lessons from building a high-performance team in a highly regulated industry & much more Timestamps: 00:02:13 Steven explains his transition from ICU and private practice to preventative medicine 00:04:31 Migrant childhood between China and Australia builds empathy and listening skills 00:14:00 Night‑shift epiphany in ICU: “we could save more lives by intervening earlier” 00:29:45 Meeting Sam Kothari and transitioning from a boutique practice into a scalable startup  00:51:22 The three pillars: nutrition, movement, rest. Which is the highest‑ROI starting point 00:58:54 Chronic sleep debt in startup life, how to measure sleep quality with objective, subjective and behavioural data 01:09:48 Dangers of visceral fat and how to reduce it 01:30:00 Seed round validation: 40,000+ biomarker data points show significant member gains 01:34:25 Balancing a high‑growth mission with fatherhood: savoring scarce moments with kids  Our partners: Thank you to Sam Kothari, Chai Ng and Kelly Huang for their help with research for this interview! A big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club: The world’s first human accelerator Steven’s links: Steven on LinkedIn Everlab People mentioned: Sam Kothari Chai Ng Bryan Johnson Alexandra Zatarain Companies mentioned: Playbook Ventures Eight Sleep Whoop Oura Fitbit Ramsay Health Care Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep217 – Dr Steven Lu (Co-founder & CMO – Everlab) on building the future of preventative health appeared first on Startup Playbook.

  • Jul 17, 2025 · 58 min

    Ep216 – Chris Withers (Founder & CEO – Klikit) on lessons from Uber & Gojek, beating cancer & solving hard problems

    My guest for Ep216 of The Startup Playbook Podcast was Chris Withers. This week marks 9 years of The Startup Playbook Podcast. What started as a side project in 2015 has now become a platform that’s shared the stories of 200+ founders, investors, and operators — and I’m so grateful to all of you who’ve tuned in, shared episodes, and supported the show along the way. To mark the milestone, I couldn’t have asked for a better guest than Chris Withers, the Founder & CEO of Klikit, a platform helping merchants grow revenue, cut costs, and streamline operations through a powerful all-in-one operating system. Before founding Klikit, Chris was part of the early Uber team in Australia & NZ, helped scale Uber Eats across Asia, and later became VP of Global Mobility at GoJek, giving him a front-row seat to some of the world’s most intense high-growth environments. Chris is also someone I’ve personally backed through Playbook Ventures. Beyond the complexity of building in Southeast Asia, what’s inspired me most is his resilience, including his fight through a cancer diagnosis just months after raising capital as a solo founder. In this episode, we dive into: The high performance cultures at Uber and Gojek and what Chris took away from each Why hard problems are worth solving His battle with cancer and what it taught him about leadership, health, and grit The realities and misconceptions about the Southeast Asian market And much more! Timestamps: 00:02:15 Chris’ background, accidental entry into Uber via a “mechanics yard” interview in Brisbane 00:04:26 Jumping to Uber Eats APAC: contrarian career move that paid off 00:07:10 Chris explains “second-order thinking” and calculated risk-taking 00:11:56 Lessons from Uber 1.0’s boundary-pushing culture of ownership 00:15:00 Inside Gojek: mission, patriotism and Nadiem Makarim’s “Pasti Ada Jalan” mantra 00:20:21 Genesis of klikit: running six virtual brands in one kitchen to test a thesis 00:24:58 Building the “pipes and rails” before the creator-commerce vision 00:29:51 Shipping fast and moving with speed 00:33:24 Going multi-region early; why Southeast Asia forces breadth and depth 00:38:26 Facing cancer diagnosis while running a venture backed startup 00:56:04 eFishery fraud fallout and Chris’s plea not to write off Asian tech Our partners: A big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club: The world’s first human accelerator Chris’ links: Chris on LinkedIn Klikit People mentioned: Travis Kalanick Paul Santos Nadiem Makarim Daniel Kahneman – Thinking Fast & Slow Jeff Bezos Ray Kroc Ben Dunphy Companies mentioned: Uber UberEats Gojek Grab Playbook Ventures TikTok Shop Shopee Lazada Amazon Google MrBeast Burger eFishery Wavemaker Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep216 – Chris Withers (Founder & CEO – Klikit) on lessons from Uber & Gojek, beating cancer & solving hard problems appeared first on Startup Playbook.

  • Jul 10, 2025 · 45 min

    Ep215 – Ben Dunphy (Co-founder & Partner – January Capital) on data-driven VC & leveraging both equity & credit for growth

    My guest for Ep215 of The Startup Playbook Podcast was Ben Dunphy. Ben is the Co-Founder and Partner of January Capital, a VC fund that invests in early stage high growth startups in the Asia Pacific region. They also run an $85M growth credit fund, offering scale-stage companies access to non-dilutive capital. I first had Ben on the show back in October 2016 and nearly a decade later, we revisit the journey and dive into:  What’s changed and what hasn’t in early stage investing How January Capital is bridging the gap between equity and debt-based financing in an innovative model The opportunities in Southeast Asia And much more! Timestamps: 00:01:17 Ben’s background: Australia-born, now leading January Capital in Singapore 00:03:16 What’s remained constant vs. what’s changed in nine years of APAC venture 00:05:26 Proving billion-dollar outcomes outside Silicon Valley and the AI paradigm shift 00:09:03 Founding January Capital: spotting gaps and launching with three partners 00:12:41 Why (and when) startups should diversify into credit alongside equity 00:19:21 Misconceptions about “one big Southeast Asia market” and the B2B focus 00:24:07 January’s data-driven deal-sourcing engine and composite talent scoring 00:27:53 Signals of exceptional founders 00:31:00 Advice on timing investor outreach and the benefits of month-long rapport-building 00:39:04 Case study: William Li’s whiteboard pitch for Akulaku and the power of clarity Our partners: Also a big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club: The world’s first human accelerator Ben’s links: Ben on LinkedIn January Capital People mentioned: Jonathan Hodson Jason Edwards William Li Companies mentioned: Akulaku ShopBack TikTok Blue Sky Venture Capital Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep215 – Ben Dunphy (Co-founder & Partner – January Capital) on data-driven VC & leveraging both equity & credit for growth appeared first on Startup Playbook.

  • Jul 3, 2025 · 57 min

    Ep214 – Pan Koutlakis (Co-founder & CEO – EatClub) on rebuilding EatClub from $0 revenue to global expansion after COVID

    My guest for Ep214 of The Startup Playbook Podcast was Pan Koutlakis. Pan is the Co-Founder and CEO of EatClub, a platform that uses dynamic pricing to help restaurants fill empty tables during off-peak hours, while passing on great deals to diners. EatClub saw remarkable growth early on, but like many in the industry, the business came to a standstill when COVID hit, with revenue dropping to zero overnight. Pan responded by drastically downsizing overheads, restructuring the company, and rebuilding momentum recently leading the business to secure an impressive $18.2 million Series A round. In this episode we covered a variety of topics including:  How he convinced industry heavyweight Marco Pierre White to come on board Navigating the uncertainty of COVID The power of setting ambitious targets Frameworks for making strategic long-term bets And much more! Timestamps: 00:01:10 Pan’s Adelaide upbringing, law-and-economics studies & first jobs in hospitality 00:08:41 Joining Rocket Internet’s ‘Suppertime’ and witnessing growth-at-all-costs firsthand 00:10:17 Founding EatClub 00:13:08 Cold-emailing Marco Pierre White, why the celebrity chef came on board 00:16:12 Structuring deals with celebrities 00:22:22 Signing the very first restaurant (on the first cold-call) and refining the MVP 00:27:58 EVP’s initial pass, eventual investment and the overnight COVID revenue crash 00:56:15 Tough cuts, shutdown of U.S. ops, and doubling-down on R&D during lockdown 00:39:32 Founder/Investor relationship 00:47:58 How he thinks about product roadmap and what features to build 00:55:07 Post-pandemic rebound, UK market entry & closing the $18.2 M Series A Our partners: A big thank you to Dan Szekely, Jonte Shaw and David Hodges for their help with this interview! Also a big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club: The world’s first human accelerator Pan’s links: Pan on LinkedIn EatClub People mentioned: Marco Pierre White David Berger Ben Tyler Matt Cantelo Daniel Szekely Jamie Oliver Gordon Ramsay Dan Szekely Jonte Shaw David Hodges Companies mentioned: EatClub EVP Suppertime Foodora Delivery Hero Rocket Internet Menulog Groupon Uber Eats Mastercard Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep214 – Pan Koutlakis (Co-founder & CEO – EatClub) on rebuilding EatClub from $0 revenue to global expansion after COVID appeared first on Startup Playbook.

  • Jun 27, 2025 · 1 hr 14 min

    Ep213 – Rob Phillpot (Co-founder – Aconex) on scaling Aconex to a $1.6B exit and launching a $50M founders fund

    My guest for Ep213 of The Startup Playbook Podcast was Rob Phillpot. Rob and his co-founder Leigh Jasper have played a huge part in shaping Australia’s tech landscape, building Aconex into one of the country’s most iconic companies, taking it public in 2014 and ultimately selling it to Oracle in 2017 for $1.6 billion. Since then, Rob has dedicated his time to advising startups, supporting philanthropy, and investing through his family office, Gravel Road Ventures. Most recently, Rob, Leigh Jasper, and A Cloud Guru founder Sam Kroonenberg teamed up to launch Glitch Capital, a $50 million founders fund backing the next generation of global tech companies. In this episode, we cover a lot of ground, including: Aconex’s journey to a $1.6B exit and overcoming multiple near-death experiences What it was like to sell a company when he didn’t want to Why advising founders is 20% strategy and 80% psychology The secrets behind building a high-performance culture Balancing big ambitions with family life What Glitch Capital looks for when backing startups And so much more. Timestamps: 00:01:50 Rob’s background 00:06:27 Meeting Leigh Jasper: did school-friends always know they’d start a company together? 00:09:15 Switching tracks: advice for people stuck in a career they don’t love 00:11:07 Startup ecosystem in 2000 and the early days of Aconex 00:13:46 Staying positive: how did Rob and Leigh keep morale when things looked bleak? 00:18:22 Strength in vulnerability 00:21:58 Cultivating Aconex’s culture and common founder mistakes 00:37:58 The real story of the Aconex sale 00:43:13 Life after the exit: what did stepping away from Aconex feel like? 00:49:48 What Rob looks for as an investor 00:58:13 80% psychology: common founder struggles Rob sees as an advisor 01:00:48 Family, fitness and cooking dinner: balancing startup life with home life 01:07:05 Philanthropy focus: why Rob created the Gravel Road Foundation and how he thinks about giving Our partners: A big thank you to Ben Leach, Andrew Barron and Bill Phillpot for their help with this interview! Also a big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club – Details here Rob’s Links: Rob on LinkedIn Glitch Capital Aconex Gravel Road Foundation Gravel Road Ventures People mentioned: Leigh Jasper Sam Kroonenburg Ben Leach Andrew Barron Simon Sinek Geoff Tarrant Companies mentioned: Oracle Multiplex McKinsey & Company Amazon Web Services Deloitte A Cloud Guru HammerTech Firmable Payapps Mr Yum Leonardo.AI Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep213 – Rob Phillpot (Co-founder – Aconex) on scaling Aconex to a $1.6B exit and launching a $50M founders fund appeared first on Startup Playbook.

  • Jun 19, 2025 · 1 hr 8 min

    Ep212 – Matt Loop (Head of Asia – Rippling) on Leadership, Hiring & Growing Iconic Tech Companies

    My guest for Ep212 of The Startup Playbook Podcast was Matt Loop. There are few people who’ve had as much influence in shaping the tech landscape in this region as Matt. He began his career at Salesforce, where he was one of their earliest hires in Australia, before going on to lead sales at LinkedIn, first in ANZ, then later as Head of Enterprise in North America. After that, he returned to Australia to take on the role of Head of Asia Pacific at Slack, helping the company scale its presence across the region. Today, Matt is the VP and Head of Asia at Rippling, a workforce management platform that’s transforming how businesses manage their people, IT, and operations. Just last month, Rippling announced a $450 million Series G round, valuing the company at $16.8 billion. In this episode, we dive into a range of topics, including: How to build and lead high-performance teams Matt’s approach to hiring and what he looks for in candidates The frameworks he uses to choose which companies to join Balancing a high-impact career with family life And so much more. Timestamps: 00:02:07 Matt’s career arc: Salesforce, LinkedIn, Slack, Rippling 00:08:45 Building Salesforce APAC 00:12:29 GTM Advice to founders 00:16:48 Leaving Salesforce: spotting comfort creep & moving to LinkedIn 00:24:27 Leadership frameworks from all his previous experiences 00:30:15 Cultivating Rippling’s high performance culture 00:35:09 Frameworks for evaluating potential career opportunities 00:46:13 Hiring “good humans” with a growth mindset 00:50:02 Networking and personal branding 00:55:13 Stepping back from the day-to-day and seeing the bigger picture 01:00:10 Finding your own version of balance Our partners: A big thank you to Katrina Loop, James Demetrios and Andrew McCarthy for their help with this interview! Also a big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club – Details here Matt’s Links: Matt on LinkedIn Rippling People mentioned: Marc Benioff Satya Nadella Mike Gamson Alyssa Merwin Cal Henderson Parker Conrad James Demetrios Andrew McCarthy Companies mentioned: Salesforce LinkedIn Slack Siebel Oracle SAP Microsoft Amazon eBay Notion Atlassian Playbook Ventures Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep212 – Matt Loop (Head of Asia – Rippling) on Leadership, Hiring & Growing Iconic Tech Companies appeared first on Startup Playbook.

  • Jun 12, 2025 · 1 hr 2 min

    Ep211 – Jodie Imam (Co-founder & CEO – Tractor Ventures) on startup exits, scaling with content and life-changing personal systems

    The Startup Playbook Podcast Insights and lessons from the world's best entrepreneurs and investors Twitter Facebook YouTube Instagram Ep211 – Jodie Imam (Co-founder & CEO – Tractor Ventures) on startup exits, scaling with content and life-changing personal systems June 12, 2025 rohitbhargava Podcast My guest for Ep211 of The Startup Playbook Podcast was Jodie Imam. Jodie is the Co-founder & CEO of Tractor Ventures, which provides non dilutive capital (between $100,000 – $1.5M) to tech enabled companies. Since launching in 2020, Tractor has deployed nearly $100M, has 230 customers and is tracking at $5M in annual revenue. Prior to this, Jodie was the Co-founder of Occasional Butler which was acquired in 2020. She was also a member of Cohort #1 of the Komo Club, and in this episode we dive into a range of areas including: Lessons from launching, growing and exiting Occasional Butler How she uses content to attract talent and customers to Tractor Ventures Systems and frameworks she utilises to manage a busy schedule between running a high growth business, multiple board seats, and a busy personal life How personal goals created through The Komo Club have had a significant impact on her number one priority in life And much more! Timestamps: 00:01:54 Jodie’s background 00:03:29 How Jodie’s childhood shaped her perspective on life and business 00:05:49 Early career: building Occasional Butler and co-working space Depo8 00:07:39 The decision to go all in on Occasional Butler 00:08:50 What Jodie would do differently second time around with Occasional Butler 00:11:36 How to build credibility as an early stage startup 00:13:47 Selling Occasional Butler to Airtasker while raising two young children 00:18:04 Founding Tractor Ventures with Matt & Aprill 00:21:11 Early days of Tractor Ventures 00:24:10 Challenges with the business, restructuring 00:28:09 Culture design: 4-day workweek, 90-day scorecard & Level-10 meetings 00:30:14 LinkedIn content engine that drives both deal flow and hiring 00:44:09 Personal goals, The Komo Club & intentional parenting 00:54:49 How Jodie structures her day and week Our partners: A big thank you to Olivia Doherty, Andrew Fitzpatrick and Matt Allen for their help with this interview! Also a big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club – Details here Jodie’s Links: Tractor Ventures Jodie on LinkedIn People mentioned: Tim Fung Matt Allen Aprill Enright Andrew Fitzpatrick Olivia Doherty Dan Siepen Bryan Williams Dean Swan Cameron Falloon Janine Allis Leona Edmiston Companies mentioned: Airtasker TaskRabbit Gumtree SBE Australia Wade Institute of Entrepreneurship University of Melbourne FinTech Australia Private Media SmartCompany Crikey The Mandarin Jim’s Mowing Innovation Bay Amazon Leona Edmiston Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here Podcast: Play in new window | Download | Embed Subscribe: RSS admin January 1, 2014 Reply Lorem ipsum dolor sit amet, consectetur adipisicing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat admin January 1, 2014 Reply Lorem ipsum dolor sit amet, consectetur adipisicing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat admin January 1, 2014 Reply Lorem ipsum dolor sit amet, consectetur adipisicing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. Copyright © 2015 - Live Composer The post Ep211 – Jodie Imam (Co-founder & CEO – Tractor Ventures) on startup exits, scaling with content and life-changing personal systems appeared first on Startup Playbook.

  • May 1, 2025 · 54 min

    Ep210 – James Fuller (Co-founder & CEO – Hnry) on turning a spreadsheet into platform processing $2.6B

    My guest for Ep210 of The Startup Playbook Podcast was James Fuller. James is the Co-founder & CEO of Hnry. Hnry automates taxes for sole traders, so they never have to think about tax again. The company started from a spreadsheet that James and his wife and Co-founder, Claire, created to solve their own problem. They shared these spreadsheets with friends who passed it on to other friends before realising that there was a real business opportunity underneath these spreadsheets. Today, Hnry has 150 staff across 3 countries, has raised over $60M in funding and processes $2.6B in payments every year in Australia and New Zealand. In this episode, we dive deep into a range of topics including: The advantages that come from being a husband and wife founding team The opportunities and challenges that come from being first to market How the value of fairness is embedded not just into their company culture, but also their pricing strategy How James and Claire have overcome some of the more challenging periods of their business, including times when they’ve both wanted to quit the business And much more! Timestamps: 1:57 James’ background. 3:19 Being co-founders and spouses: pros, cons, and how they navigate disagreements. 12:29 Hnry’s growth over the years: 150 staff, 3 countries, billions of dollars processed. 18:13 Customer led product development, building trust over time, high referral rates and strong NPS as proof points. 22:43 Overcoming traditional industry challenges, educating the market about a “new category” of full-stack service. 32:43 Fairness & Hnry’s Unique Pricing Model. 38:37 Culture & team building across three countries 42:53 Balancing parenthood and startup life Our partners: A big thank you to Karan Anand for his help with this interview! Also a big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club – Details here James’ Links: Hnry James on LinkedIn People mentioned: Claire Fuller Karan Anand Vinny Pujji Companies mentioned: Xero Left Lane Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep210 – James Fuller (Co-founder & CEO – Hnry) on turning a spreadsheet into platform processing $2.6B appeared first on Startup Playbook.

  • Apr 2, 2025 · 1 hr 13 min

    Ep209 – Mathew Ellis (Co-founder & CTO – Kismet) on vertical ownership and high performing teams

    My guest for Ep209 of The Startup Playbook Podcast was Mat Ellis. This episode is a little special. Not only is it Mat’s first-ever podcast interview, but we’ve also been close friends since grade 7. And many years ago, after months of trying, I finally convinced him to join as one of the co-founders of my first startup, StageLabel. But Mat’s not on the show just because we’re friends. He’s genuinely one of the best engineers in the country. He’s the Co-founder and CTO of Kismet Healthcare, a company tackling the deep inefficiencies in healthcare and disability services. Kismet has seen phenomenal growth in just a short period of time, scaling quickly with a small, high-performing team of 30 – including an engineering team of just five. At Playbook Ventures, we were lucky enough to back Kismet from the pre-seed stage and have had a front-row seat to their incredible growth. In this episode, we unpack some of the principles behind that growth, including: Why smaller teams get more done The 2 core values that make hires successful at Kismet The importance of vertical ownership Why every engineer on Matt’s team spends one day a month on customer support calls And much more. Toward the end of the episode, we also get personal and reflect on the growth we’ve both had across all areas of our lives. Mat’s also a member of Cohort #1 of The Komo Club, where we go deep on these exact themes, exploring how to build not just high-performing businesses, but high-performing lives. If you want to find out more, check out TheKomoClub.com Timestamps: 2:29 Mathew’s background and early interest in software 4:36 Discovering startups and autonomy 7:41 StageLabel and lessons in ownership 9:54 The importance of doing something you like 11:54 Lessons from early in his career that he applies now at Kismet 18:33 Transition to Xplor 23:53 Co-founding Kismet 31:09 Scaling with small, high trust teams, why vertical ownership (end-to-end accountability) drives better outcomes 39:32 Hiring for culture fit at Kismet: humility and ownership and what to look for in technical talent 43:54 Why Kismet does its best to scare people off in interviews 49:25 Overcoming challenges of scale and the sacrifice you make when starting a company 55:31 Personal Growth: From work first to a balanced life, how a holistic approach improves work performance 1:02:50 How Mat has stopped being a passenger in his own life 1:05:40 How taking care of himself properly allows him to perform better at work Our partners: A big thank you to Mark Woodland, Harry Travers and Bejoy Machumpurath for their help with this interview! Also a big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club – Details here Mathew’s Links: Kismet Mat on LinkedIn Kismet’s email People mentioned: Mark Woodland James Chin-Moody David Goggins Jocko Willink Jason Fried Companies mentioned: StageLabel Department of Defense Lockheed Martin Xplor Playbook Ventures Sendle Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep209 – Mathew Ellis (Co-founder & CTO – Kismet) on vertical ownership and high performing teams appeared first on Startup Playbook.

  • Mar 26, 2025 · 1 hr 29 min

    Ep208 – Jane Martino (Co-founder & Chair – Smiling Mind) on founder mental health, mindfulness & multiple exits

    My guest for Ep208 of The Startup Playbook Podcast was Jane Martino. Jane has had an incredibly successful career as a director, investor, advisor and founder of a number of companies that have successfully exited. She’s best known as the Co-founder & Chair of Smiling Mind, one of the worlds leading mindfulness and mental health tools with over 9.3M downloads and 14M young people reached globally. She now helps individuals reach their maximum potential through her coaching business, Kintsugi Way. In this episode, we cover: Lessons from launching, scaling and exiting several businesses The role of good advisors and board members How to deal with co-founder conflicts How to deal with emotions and stress as a founder And much more. PS we go deep into several important topics in this episode and they are just some of the topics we dive into at The Komo Club. The Komo Club is a private program I’ve launched for high-performing founders, operators and executives who want to win not just in business, but across all areas of life—from health and relationships to personal growth and leadership. It’s an 8-week cohort experience that combines world class content, practical systems and frameworks a curated community to help you reach your goals. And I’m incredibly proud to share that Jane will be joining us as one of the featured guest speakers for the upcoming cohort. She’ll be diving deeper into the frameworks and lessons she’s used to lead with purpose, avoid burnout, and create lasting impact; personally and professionally. If this episode resonates with you, I think you’ll love what Jane will be sharing inside The Komo Club as well. Cohort 1 applications are now open. You can learn more at TheKomoClub.com or by reaching out to me directly at rohit@startupplaybook.co. Timestamps: 3:07 Janey’s background 13:49 Founder mental health 18:59 Experience with meditation and practical uses for business 24:27 Communicating with co-founders and colleagues 35:33 How she applied these to the situation at Unlockd 45:40 Thoughts on hustle culture 56:48 How she’s approached being a founder 59:30 Her approach to advisory roles 1:09:58 How she helps co founders decide on the roles they’ll play in the business 1:20:55 The journey with Smiling Mind Our partners: A big thank you to Laura Henshaw and Andrew Duncan for their help with this interview! Also a big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club – Details & Cohort #1 applications available here Janey’s links: Jane on LinkedIn Kintsugi Way Smiling Mind People mentioned: Rachael Neumann Robin Sharma James Tutton Laura Henshaw Companies mentioned: Unlockd AWS CSIRO Aussie Founders Club Boost Mobile Tesco Mobile Google Kic DiSC profile Headspace Calm Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here https://youtu.be/JZ9chMylhxA The post Ep208 – Jane Martino (Co-founder & Chair – Smiling Mind) on founder mental health, mindfulness & multiple exits appeared first on Startup Playbook.

  • Feb 27, 2025 · 1 hr 17 min

    Ep207 – Dean Swan (VP for APJ at Monday.com) on growing Monday.com zero to $100M+ in APJ

    My guest for Ep207 of The Startup Playbook Podcast was the Vice President and General Manager for Asia-Pacific & Japan at Monday.com, Dean Swan. Dean spent 11 years at Microsoft before becoming the Country Manager for Australia & New Zealand at Dropbox. He’s now the Vice President and General Manager of APJ at Monday.com. When Dean joined Monday.com as the first hire in the region, he set an audacious goal: to grow his part of the business to $100 million in 5 years – an ambitious target considering the entire company was valued at $120 million at the time. Fast forward to today, he’s grown the team to 140 people and is just $2 million shy of that $100 million target – months ahead of schedule. In 2021, Monday.com went public and now boasts a market cap of $15.97 billion. In this episode we covered a variety of topics including:  How to effectively expand into new markets and territories How to hire and attract the best talent How Dean grew the business from zero to $100M in the APJ region The steps he takes to perform at his best, which led to him losing 20kg+ And much more! Timestamps: 3:38 Dean’s background 5:19 Early career experiences as a chef 9:12 Transitioning into technology 11:02 Learnings from 11 years at Microsoft 16:04 How to build culture in a company 21:35 His experience expanding Dropbox and monday.com into other markets 30:58 His own entrepreneurial journey prior to Dropbox & monday.com 38:22 Balancing vision with daily focus 42:18 Why he left Dropbox to help build out monday.com in APJ, early challenges 46:23 How he looks for and attracts talent 52.47 His initial growth plans for monday.com 59:33 Thoughts on AI and how he’s using it personally and at monday.com 1:06:56 The catalyst that made him prioritise his health and lose 20kg Our partners: A big thank you to Greg Walsom help his help with this interview! Also a big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. The Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/podcast to get access to this exclusive discount. Links mentioned: The Komo Club – Details & Cohort #1 applications available here Dean’s Links: Dean on LinkedIn monday.com People mentioned: Bill Gates Steve Balmer Satya Nadella Roy Mann Eran Zinman Greg Walsom Adam Schwab David Shein Companies mentioned: Microsoft Dropbox Google Hum Technologies Amazon G2 Luxury Escapes Tourism Australia Canva OpenAI Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep207 – Dean Swan (VP for APJ at Monday.com) on growing Monday.com zero to $100M+ in APJ appeared first on Startup Playbook.

  • Feb 12, 2025 · 1 hr 3 min

    Ep206 – Adam Schwab (Co-founder & CEO – Luxury Escapes) on reinventing Luxury Escapes & Scaling to $1B+ GTV

    My guest for Ep206 of The Startup Playbook Podcast was Adam Schwab. Adam started his career as a lawyer before transitioning to startups and has had a number of successful businesses, but is best known as the Co-founder & CEO of Luxury Escapes. Luxury Escapes is one of the world’s leading travel brands, revolutionising the way people book luxury getaways. Despite their success, it hasn’t always been a straightforward journey for the company, particularly going through periods such as COVID (an extremely difficult time for all travel businesses) and with Adam stepping away from the CEO role for a period of time. However he stepped back in the role with a renewed vision of the company and has seen the business grow from $350M pre-COVID to now doing over $1B in GTV sales annually. In this episode we covered a variety of topics including: Why Adam no longer looks at acquisitions as a growth strategy Why stepping away from Luxury Escapes made him a 10X better CEO The pivot in the business led to them growing from $350 million GTV to $1 billion+ GTV And much more! Timestamps: 3:05 Adam’s background 7:10 Early entrepreneurial journey, inherent traits and developed skills that helped him 9:39 Lessons from first business 13:14 Initial growth strategies at Luxury Escapes 18:50 Getting sued by Gabby & Hessi and then doing JV deals with them 25:23 Pivoting the business model 29:11 Creating culture and hiring at scale 33:45 Barefoot running 35:14 Understanding the needs of the customer and market 37:33 Leaving Luxury Escapes 43:41 Playing offense instead of defence during COVID as a travel company 48:55 the choice to limit outside funding 50:49 Key business metrics he tracks at Luxury Escapes 52:06 Future plans for Luxury Escapes 55:44 The changes he made coming back to Luxury Escapes after leaving 58:25 Taking care of health 1:00:28 How life priorities shift over time Our partners: A big thank you to Jeremy Sane and Shay Hamama for their help with this interview! Also a big shout out to our long-term partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/playbook to get access to this exclusive discount. Links mentioned: The Komo Club – Details & Cohort #1 applications available here Adam’s Links: Adam’s LinkedIn The Contrarians with Adam and Adir Luxury Escapes People mentioned: Jeremy Same Evan Spiegel Elon Musk Mark Zuckerberg Warren Buffet Mike Sneesby Steve Jobs Gabby Leibovich Hezi Leibovich Mark Hoenig Joshua Landy Chris McDougall Jensen Huang Shay Hamama Campbell McComb  Hamilton Helmer Jeff Bezos Adir Shiffman Companies mentioned: AirBnB OpenTable Groupon Herbert Smith Freehills Nine Microsoft LivingSocial eBay Scoopon Menulog Wesfarmers Catch.com.au Amazon Expedia Trip Auctus Investment Group Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep206 – Adam Schwab (Co-founder & CEO – Luxury Escapes) on reinventing Luxury Escapes & Scaling to $1B+ GTV appeared first on Startup Playbook.

  • Jan 30, 2025 · 1 hr 5 min

    Ep205 – Damir Cuca (Founder & CEO – Basiq) on building and exiting 2x startups and being a father of six

    My guest for Ep205 of The Startup Playbook Podcast was Damir Cuca. From tinkering with toys and electronics and immigrating to Australia as a child without knowing the language to building and exiting two successful businesses, Damir’s career has been a masterclass in determination, resilience and growth. He’s best known as the Founder & CEO of Basiq, an Open Banking platform that offers secure access to consumer financial data. Basiq went on to raise several funding rounds from top-tier strategic investors in the space including Salesforce Ventures, NAB Ventures and Westpac’s Reinventure fund before being acquired by payments giant, Cuscal, in 2023.  How to design a company culture that thrives on competitiveness and performance What the process of acquisition looks like and what it meant for him personally How he balances having an ambitious career with being a husband and a father to six children And much more! Timestamps: 1:28 Damir’s background 10:14 Pivoting from a blue collar path to software engineering 17:49 Building a technical and commercial skill set 25:18 Tips on defining problems to focus on in business 29:34 Moving to Serbia to set up Basiq 37:15 Building the culture at Basiq 41:41 Instilling continuous learning mindset 44:17 When to fight and when to let go 48:56 How he approached fundraising and the acquisition process 54:32 The experience of going through the exit 58:45 How he thinks about raising his 6 kids Our partners: A big thank you to Rohen Sood, Jake Osborne, Victor Leung and Elizabeth Cuca for their help with this interview! Also a big shout out to our partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/playbook to get access to this exclusive discount. Links mentioned: Damir’s links: Damir’s LinkedIn People mentioned: Rohen Sood  Victor Leung Jake Osborne Steve Jobs Companies mentioned: Basiq  Salesforce Ventures NAB Ventures Reinventure Cuscal Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep205 – Damir Cuca (Founder & CEO – Basiq) on building and exiting 2x startups and being a father of six appeared first on Startup Playbook.

  • Jan 23, 2025 · 1 hr 3 min

    Ep204 – George Hartley (Co-founder & Co-CEO – Bluethumb) on lessons from building a $100M art marketplace

    My guest for Ep204 of The Startup Playbook Podcast was George Hartley. George is the Co-founder & Co-CEO of Bluethumb, Australia’s largest art marketplace. Since its launch in 2012, Bluethumb has grown into the leading art marketplace platform, connecting over 23,000 artists with buyers and selling more than $100 million worth of artwork. In addition to Bluethumb, George was also the Co-founder and CEO of SmartrMail, an email marketing platform designed to help e-commerce businesses delight their customers and boost sales. SmartrMail’s success led to its acquisition by Relay Commerce in 2022, delivering a 5x return to its seed investors. In this episode, George shares insights into: Why Bluethumb waited three years to raise their seed round and why they’ve stayed bootstrapped since The importance of continuously taking risks and experimenting to drive growth The unique challenges and strategies for scaling consumer marketplaces versus SaaS companies Timestamps: 1:49 George’s background 7:30 His journey from music to tech 11:33 How to know when to stick with something vs pivot 15:45 The early days of Bluethumb 19:52 Staying true to your vision despite external noise 24:18 The fundraising journey for Bluethumb 32:03 The SmarterMail journey 38:02 Identifying and hiring talent 45:34 How he thinks about taking risks and running experiments 52:54 US Expansion Our partners: A big thank you to Freddy Grant and Ed Hartley for their help with this interview! Also a big shout out to our partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/playbook to get access to this exclusive discount. Links mentioned: George’s links: George on LinkedIn Bluethumb Bluethumb on Instagram Art in my Home Podcast People mentioned: Steve Jobs Richard Branson Edward Hartley Philip Slusarski Bradford D. Smart – Topgrading Freddy Grant Lorenzo Ghiberti Companies mentioned: Costco Apple SoundCloud Luxury Escapes Zappos Startmate SmartrMail LivingSocial EVP Klayvio Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep204 – George Hartley (Co-founder & Co-CEO – Bluethumb) on lessons from building a $100M art marketplace appeared first on Startup Playbook.

  • Jan 16, 2025 · 1 hr 9 min

    Ep203 – Ben Pfisterer (Co-founder & CEO – Zeller) on becoming the fastest Australian company to achieve unicorn status

    My guest for Ep203 of The Startup Playbook Podcast is the Co-founder & CEO of Zeller, Ben Pfisterer. Ben is a returning guest on the show. Our last interview was in August 2020 when Ben had left his role as Country Manager for Square to launch his new company, Zeller, which had just come out of stealth mode to announce their $6.3M funding round. Since then Zeller has become the fastest Australian company to a $1B valuation, reaching that milestone in less than 2 years. Zeller has 85,000 customers, 260 staff and to date has raised $180M in funding from leading investors. In this interview we covered a range of topics including: The challenges that come with scale How raising capital changes from Seed to Series B stage How hiring and company culture evolves as you scale the company Why Ben doesn’t do any one-on-ones with any of his direct reports And much more! Timestamps: 2:06: Ben’s background 7:09: How to find your path in career 8:36: The background of Zeller 11:05: The storytelling aspect of raising capital 15:07: The unexpected challenges that came from taking on the big banks 21:05: How transparent should you be with your company and investors? 23:22: Hiring talents and maintaining culture as you scale 39:19: How he thinks about product at Zeller 47:41: How he’s worked with investors as Zeller grows 56:50: How he structures his time 1:01:21: The horizon theory 1:05:07: The mission and objective with Zeller 1:06:17: How he’s found his own balance with work and life Our partners: A big thank you to Josh McNichol for his with this interview! Also a big shout out to our partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/playbook to get access to this exclusive discount. Links mentioned: Ben’s links: Ben’s LinkedIn Zeller Zeller roles People mentioned: Mark Woodland Dominic Yap Josh McNicol Companies mentioned: Square NAB Siemens Hewlett-Packard Square Peg Capital Kismet Apex Capital Partners Headline Spark Capital Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep203 – Ben Pfisterer (Co-founder & CEO – Zeller) on becoming the fastest Australian company to achieve unicorn status appeared first on Startup Playbook.

  • Dec 19, 2024 · 57 min

    Ep202 – Josh Ball (Co-founder – Farmers Pick) on using tech to save 7 million kg of food waste

    My guest for Ep202 of The Startup Playbook Podcast was the Co-founder of Farmers Pick, Josh Ball. Farmers Pick helps save food waste by rescuing wonky food that is often discarded by supermarkets and making it available to order by consumers. Since launching in 2020, they have saved 7 million kilograms of produce and the company now has 120 employees and generated $16M in revenue last year. In this interview we covered a range of topics including: The importance of having a strong mission and values to help guide strategic business decisions balancing frugality with 100% YoY growth Why they decided to go down the equity crowdfunding path rather than raising from traditional VC funds Scaling storytelling to both their staff and to their customers And much more! Timestamps: 1:45 Josh’s background 7:12 The origin story of Farmers Pick 12:29 How he validated the initial idea 18:27 The operational complexities of growing a physical goods business 27:52 Finding the balance between focussing on new customers vs expansion of existing customers 29:50 Using social media to grow the brand 31:05 The decision to crowdfund vs raise venture capital 35:29 Negotiation advice 37:41 Making sure the vision/mission stays consistent across whole company as you grow 42:43 Thinking about expansion 48:04 How his role has evolved as the business has grown 54:00 Staying out of the weeds and making strategic decisions 55:40 What’s next for Farmers Pick Our partners: A big thank you to our partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/playbook to get access to this exclusive discount. Links mentioned: Josh’s links: Josh’s LinkedIn Farmers Pick People mentioned: Joshua Brooks-Duncan Simon Griffiths Adrian Osman Companies mentioned: PromisePay Xero Misfits Market Who Gives A Crap MILKRUN Playbook Ventures me&u Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep202 – Josh Ball (Co-founder – Farmers Pick) on using tech to save 7 million kg of food waste appeared first on Startup Playbook.

  • Dec 12, 2024 · 1 hr 14 min

    Ep201 – Cheryl Mack (Co-founder & CEO – Aussie Angels) on how to get started as an angel investor

    My guest for Ep201 of The Startup Playbook Podcast was Cheryl Mack. Cheryl started her journey launching and growing Startcon, which was Australia’s largest startup conference at the time. She’s now involved with a number of different projects including The Pillars, 361 Angel Club and the First Cheque Podcast but she is best known as the Co-founder & CEO of Aussie Angels. Aussie Angels is a platform that manages the backend infrastructure of investments, allowing angel investors to invest in startups via syndicates. To date, over 1,700 angels have invested $23M through their platform. In this interview we covered a range of topics including: The importance of brand, marketing and storytelling How to get started with angel investing What founders should look for when adding angel investors to their cap table What investors really mean when they say they look for “good” founders, markets and investment opportunities & much more! Timestamps: 1:43 Cheryl’s background 3:54 Growing up in Canada and moving to Australia 8:25 Building StartCon, Australia’s biggest startup conference in Australia at the time 14:31 Choosing themes/sectors as an Angel Investor 20:49 What Cheryl looks for when personally investing in companies 29:26 Learnings from early mistakes as a new Angel Investor 35:41 Advice for new Angel Investors 38:00 Benefits of joining a syndicate 47:43 How founders should think about taking money from angel investors 54:06 Signals investors should look for when deciding whether to invest 1:00:44 Challenges and benefits of working with your partner, balancing family life 1:10:13 Redistributing wasted toys Our partners: A big thank you to Tom Worden and Alexandra Lewis for their help with this interview! Also a big shout out to our partners for the show: Scendar Scendar is the OG startup accounting firm in Australia catering to all stages of your business’ life. If you’re busy running your startup, you don’t have time to do your own books and forecast. Instead, fully outsource your finance function, giving you time and resources back to focus on what you do best in growing your business. Find out more at Scendar.com Vanta Vanta helps businesses get — and stay — compliant by automating up to 90% of the work for the most in-demand compliance frameworks. And with over 300 integrations, you can easily monitor and secure the tools your business relies on. Join over six thousand fast-growing companies that use Vanta to manage risk and prove security in real time. Startup Playbook Podcast listeners get access to an exclusive offer of USD$1000 off their plans. Head over to vanta.com/playbook to get access to this exclusive discount. Links mentioned: Cheryl’s links: Cheryl’s LinkedIn Aussie Angels The Pillars 361 Angel Club First Cheque Podcast People mentioned: Mike Cannon-Brookes Matt Barrie Rod Drury James Harrisson Thomas Worden Adrian Osman Cliff Obrecht Melanie Perkins Alexandra Lewis Companies mentioned: StartCon The Startup Network (formally Startup Victoria) Freelancer Xero Airtree Blackbird Playbook Ventures AWS Cut Through Venture me&u (formally Mr Yum) Feedback/connect/say hello: Rohit@startupplaybook.co @RohitBhargava7 (Twitter) /rohbhargava (LinkedIn) @rohit_bhargava (Instagram) My Youtube Channel Credits: Music: Paycheck Other channels: Find all of the links for the podcast on Linktree here The post Ep201 – Cheryl Mack (Co-founder & CEO – Aussie Angels) on how to get started as an angel investor appeared first on Startup Playbook.