Bootstrap Podcasts
Welcome to Bootstrap Confidential the podcast by bootstrappers for bootstrappers giving you a playbook on how to build and successfully bootstrap a business. Every episode I chat with successful bootstrappers about their journey, their stories, their passions, the fun they’ve had and most importantly the lessons they’ve learned.
We’ll chat about what worked and didn’t work, the lessons they’ve learned and how to succeed giving you, our listeners, all the tools, ideas and thoughts that you need for your own bootstrapping journey
Episode 1- The man who sold his parachute to bootstrap an $88M business
Episode 2- The 21 yr old model who went from walking the runway to building her own
Episode 3- The man who bootstrapped a billion dollar fintech
Episode 4- Walking into Wired's office in Silicon Valley at the start of the internet he quit his job, bootstrapped a business and transformed it radically 5 times in 30 years
Episode 5- 'It was the best of times. It was the worst of times'
From selling horse manure in London to founding a business selling digital wealth in Asia listen to our latest episode as we chat to Ned Phillips aka the salesman
Episode 6- Not only did Karmo founder Nick Boucher start and build his own business he also created a brand new industry vertical which he now dominates. Listen to his story
Episode 7- Angus Stevens, co-founder of Start Beyond, narrowly cheated death in a hang gliding accident and promised himself to make each day count. Listen as he talks about founding and building Start Beyond over the last ten years
Episode 8- In 2013 Samantha Dybac was $80k in debt, battered and bruised from her latest business venture and in need of a break. Less than 6 months later she founded The PR Hub, successfully building and bootstrapping it into the leading agency it is today. Listen as the 4 x founder talks incredibly honestly and openly about building a business as a single mum, mental resilience and the constant drive of a founder
Episode 9- After 25 years in a highly successful corporate career Olivia Leong, to the consternation of her Mum, decided to jump ship and start her own business. Listen as she discuss making the leap from corporate life
Episode 10- Successful 2 x founder Jane Bianchini trekked to Everest Base Camp with her children to get a contract signed to help launch her first business. Out of that first success as a non-tech founder she spun a tech solution that created a brand new market. Listen as she discusses Razorblades and Champagne
Episode 11-In 2016 as Insuretech was born Matthew Grant was at the forefront building a community of the curious, working out how to monetise it and bootstrapping it to a successful exit in 2025.
Episode 12- Sophie Bruce is a qualified sports psychologist and has sat at the top table with founders numerous times. However becoming a Mum and parent highlighted a problem that needed solving and inspired her to take the plunge herself founding and bootstrapping MOLO App. Listen as she discusses her journey
Episode 13-- In 2014 Mohit Sagar was understandably shocked to discover he had been let go via a Linkedin public post. Deciding to seize the moment be founded and successfully bootstrapped OpenGov Asia. Listen as he discusses all the lessons he's learned over the last decade
Episode 14- With not 1 but 5 entrepreneurial uncles it was always in Victor Cruz's blood to launch a business, prompting him to found VC Innovations just before the pandemic. Listen as he talks about the lessons from this and how he built the UK's No1 fintech event, pivoting on a dime, dealing with extreme external events, superpowers, resilience, being agile and most importantly creating a valuable solution to an industry problem
Episode 15- The Future of AI and Start Ups- what every founder needs to now. Listen as Charles Green talks to Brett King, top 10 global futurist, best selling author, fonder and Fintech Hall of fame member about what AI can mean and the opportunities it brings to founders
Episode 16- After 7 years of witnessing the same data problem and presuming someone else will fix it Lauren Murphy and Emma Dunn decided to leave their successful corporate careers and take the plunge, founding a data governance and cyber security business. Now 18 months in and with a small but growing team, revenue streams and a successful product listen as they talk about getting started, building runway, what bootstrapping has taught them, building a product, what has surprised them and all the lessons they've learned
Episode 17- Turning 30, Piers Bearne decided it was now or never to launch a startup. However as one startup success led to another and he learnt more and more about founding and scaling businesses he spotted yet another opportunity. Listen as Charles Green talks with him about all he has learnt in the last 30 years on the joys and challenges of founding and most importantly scaling
Episode 18- Having learnt the value of collecting hard data by visiting offshore weather buoys off the continental shelf in the North Atlantic for the UK met office, Helen Tanner, then saw an opportunity to provide real data value and monetisation to businesses, founding Data Cubed.
Episode 19- Multiple founder John Baskott learnt the value of co-founders in his first startup aged only 25, so made sure he had cofounders for his next successful startup as he built it up to an 8 figure exit. Listen as he and Charles Green discuss co-founders, sales strategies and team balance, high performance cultures, vision and clarity
Episode 20 -Motherhood and children often means stepping back from work but Jennie Moss saw it as the perfect opportunity to bootstrap a business from her kitchen table, building it up over 14 years to a successful exit. Listen as Charles Green and her talk about why bootstrap, who to hire, how to scale, the reality of founder life, the challenges and lessons and much more