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Home/The SaaS Podcast/10 Software Entrepreneurs Share Their Best Business Advice
10 Software Entrepreneurs Share Their Best Business Advice
Bootstrapping

10 Software Entrepreneurs Share Their Best Business Advice

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Dan Norris is co-founder of WP Curve, one of the world’s fastest-growing WordPress support companies. He’s an entrepreneur with an obsession for content marketing and was voted Australia’s top small business blogger by ‘Smarter Business Ideas’, Australia’s largest business magazine. He’s also the author of ‘The 7 Day Startup: You Don’t Learn Until You Launch’.

Trevor Owens is an author and entrepreneur. He’s the co-founder and CEO of Javelin.com – the makers of QuickMVP and Lean Startup Machine. QuickMVP is a service that lets you quickly and easily test business ideas. And the Lean Startup Machine is workshop that teaches you how to build something customers want and run the right experiments to steer your business in the right direction. Trevor is also the author of the book, The Lean Enterprise, which details how corporations can apply more innovation and Lean Startup to launching new products.

Paul Graham is a programmer, writer, and investor. In 1995, he and Robert Morris started Viaweb, the first software as a service company. Viaweb was acquired by Yahoo in 1998, where it became Yahoo Store. In 2001 he started publishing essays on paulgraham.com, which in 2014 got 12 million page views. In 2005 he and Jessica Livingston, Robert Morris, and Trevor Blackwell started Y Combinator, the first of a new type of startup incubator. Since 2005 Y Combinator has funded over 800 startups, including Dropbox, Airbnb, Stripe, and Reddit.

Rob Walling is the founder of email marketing tool Drip and the owner of SEO keyword tool HitTail. He’s also the author of the book “Start Small, Stay Small: A Developer’s Guide to Launching a Startup”. And his blog “Software by Rob” is a top 20 startup blog and is read by about 20,000 web entrepreneurs each month.

Wade Foster is the CEO and co-founder of Y-Combinator startup Zapier. Zapier lets SaaS users create integrations that push data between hundreds of best-in-breed web apps without having to write any code or deal with APIs.

Peter Coppinger is the Co-Founder & CEO of Teamwork, an online collaboration tool that allows teams to work together more efficiently. Peter and his co-founder Daniel Mackey founded the Irish based company in 2007. Peter and Daniel have bootstrapped the company and to date Teamwork has almost 1.5 million users and $14M in annual revenue.

Andrew Wilkinson is the founder of MetaLab and Flow. Metalab is a design agency that Andrew founded when he was just 20 years old and has grown it into a business with over 60 employees. MetaLab is the design team behind Slack which is now valued at $2.8 billion. And Flow is a task management SaaS application for teams which is used by companies like Etsy, Tesla, Adobe, and TED.

Tom Leung is the co-founder and CEO of Anthology, a Seattle-based startup that was formerly known as Poachable. Anthology enables employed tech professionals to explore new career opportunities anonymously. The company has raised around $1.8 million to date and its investors include Vulcan Ventures. And companies recruiting through Anthology include Amazon, Microsoft, Netflix, Dropbox, Facebook and around 100 venture-backed startups.

Steli Efti is the co-founder and CEO of Close.io, a Y Combinator startup that helps to improve communication and customer management for salespeople.

Omer Khan is the founder of SaaS Club and host of The SaaS Podcast.  SaaS Club is an online community for early stage SaaS founders and software entrepreneurs. The SaaS Podcast helps founders to build, launch and grow successful SaaS products. Previously, Omer was director of product management at Microsoft working on the Bing search engine.

This episode is part of our Bootstrapping series.

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More on Bootstrapping

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Adam Fard, UX Pilot

Bootstrapped SaaS: From Agency to $5M ARR in 2 Years

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Bootstrapped SaaS to 8-Figure Exit (No VC, No Problem) - James Ashford

James Ashford, GoProposal

Bootstrapped SaaS to 8-Figure Exit (No VC, No Problem)

James Ashford is the founder of GoProposal, a proposal and pricing platform for accountants which he bootstrapped and sold for an 8-figure sum. James didn't have a tech background. He wasn't an accountant. And he'd never built software before. But he noticed something broken: accountants couldn't price their services. They'd guess fees based on what the last client paid. Proposals took days. Deals fell through because people got busy. So he built a simple solution. A digital menu that let any staff member price and close deals in 15 minutes. The first version? A WordPress plugin that cost £4,000 to build. Before writing a single line of code, James did something unusual. He calculated how much money he needed to never work again (£5 million), identified the companies that might acquire his business (Sage, Intuit, Xero), and printed their logos on his wall. This wasn't optimism—it was his bootstrapped SaaS exit strategy from day one. To crack the accounting industry as an outsider, he traded 10% of his software company for 10% of an accounting firm. Instant credibility. Then he wrote a book in two weeks, made it an Amazon bestseller, and used it to build a waitlist of hundreds before launch. His marketing philosophy was simple: market like a celebrity chef. Gordon Ramsay shows you how to cook his recipes for free. You still go to his restaurant. James gave away everything—the methodology, the frameworks, the exact playbook. People still bought the software because they wanted it done faster. The bootstrapped SaaS approach forced creativity. When he realized a single conference cost £25,000, he hired a full-time videographer instead. Twelve months later, the pandemic hit. Competitors who relied on events were stuck. GoProposal dominated online. By the time he sold, GoProposal had over 1,100 customers, a 78 NPS score, and playbooks for every single process in the business. Three potential acquirers approached him within months of each other. The exit price? 8 figures. The multiple? One he still doesn't publicly share because it was "crazy."

Bootstrapped SaaS to $30M ARR: Why Scarcity Forces Focus - Sam Darawish

Sam Darawish, Everflow

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