#115: Living Abroad While Bootstrapping, with Craig Hewitt

Craig and I are both bootstrapping our businesses while living in foreign countries. In this episode we discuss what that’s like for us personally. We also discuss the challenging practicalities of visas, languages, and business while living abroad.

Thanks to Balsamiq who sponsored this episode. Find out how, thanks to Balsamiq, you can promote your bootstrapped business for free on the podcast.

We also discuss:

  • Craig’s efforts with paid acquisition
  • how Steve refined the sign-up process for Feature Upvote

#114: “The Tables are Turned”, with Craig Hewitt

Craig turns the tables and interviews me about Feature Upvote and about this podcast.

We discuss:

  • why Steve launched Feature Upvote when he already had a successful product.
  • doing things differently the second time around.
  • the beauty of “expansion revenue”.
  • B2C vs B2B (spoiler alert: B2B has a whole lot of advantages).
  • the Bootstrapped podcast 10 episodes into its new iteration.

#113: “The idea of public speaking fills me with unspeakable terror”, featuring Craig Hewitt

We discuss how you can become a speaker at events, and whether this is a viable way to raise awareness of your product and services.

Topics include:

#112: Three ways to use podcasts for marketing. Featuring Craig Hewitt, founder of Castos

Craig and I discuss how bootstrappers can use the podcasting ecosystem to promote their products.

We discuss three ways to use podcasts – and the pros and cons of each:

  1. Start and run your own podcast
  2. Do the “podcast circuit” as an interesting guest with riveting insights
  3. Sponsor podcasts

We ‘go meta’ and talk about why Steve has launched the new iteration of the Bootstrapped podcast.

We also talk about:

  • “credit card required upfront” trials versus “no credit card required” trials.
  • the life-cycle email sequences using activity-based triggers that we’ve recently added to Feature Upvote.
  • the danger of applying data-based marketing approaches to products when your product doesn’t have enough data
  • why Steve doesn’t do A/B testing – yet

#111: “Should I apply for TinySeed?” with Craig Hewitt, founder of Castos

I’m joined by Craig Hewitt for the first of several episodes in which he is my cohost.

TinySeed is a “startup accelerator designed for bootstrappers.” Craig was accepted into TinySeed’s first cohort.

To help me answer the question, “Should I apply for TinySeed?”, Craig tells me what it has been like for him. We discuss why he applied, how it has changed his business so far, and what unexpected benefits there are have been.


#110: “Living the Bootstrapper dream” with Robin Warren, founder of Corrello

Robin and I discuss living the Bootstrapper dream – and how the dream changes over time. We also go off topic and discuss surfing up the Bristol Channel.


#109 – Andy Brice – Founder of EasyDataTransform

Andy and I discuss why he’s created a new product, even though he already has two successful products.

We also discuss:

  • how Andy manages a portfolio of three desktop apps as a one-person team
  • how to name products
  • choosing a market
  • usability testing
  • choosing to remain a one-person team
  • the benefits of the founder doing customer support
  • why many one-person businesses are actually two-people businesses


#108 – Hannah Adcock – Owner of Contented Strategy

Hannah and I discuss content strategy for bootstrappers.

Hannah’s website: https://contentedstrategy.com/

Hannah’s book: “Content Strategy for Solopreneurs, Startups, Charities and Growing Businesses”: https://contentedstrategy.com/content_strategy_for_startups.html

How to do a content audit: https://contentedstrategy.com/blog/2019/05/17/startup-content-audit.html

Traction by Gabriel Weinberg: https://www.amazon.com/Traction-Startup-Achieve-Explosive-Customer/dp/1591848369

#107 – Robert Brandl – Founder of WebsiteToolTester

Robert and I discuss how to hire and manage freelancers. We also discuss how having children forces you to change the way you work.

Robert’s 4 tips for a healthy freelancer relationship:

  1. Meet in person from time to time, if possible
  2. Pay at the higher end of their expected rate
  3. Remember the Golden Rule: Treat them they way you expect to be treated
  4. Let them know the positive results of their work


#106 – Sylvestre Dupont – Cofounder of Parseur

In my conversation with Sylvestre from Parseur, we discuss how bootstrapping allowed Sylvestre to move to Mauritius. We also discuss:

  • Collecting domain names
  • Leaving consulting to bootstrap a SaaS
  • Bootstrapping with the generous assistance of the French government(!)
  • The tough months before the first sale – and then the elation after the first sale
  • Using Quora to land the first customers – and to learn the language used by your potential customers
  • Using Zapier for leads
  • The difficulty of opening a Dutch company when you don’t speak Dutch
  • Choosing a place to live when you work remotely
  • The challenges and rewards of bootstrapping from Mauritius
  • Translating your website for SEO gains
  • Travelling the world by cargo ship
  • Supporting customers from a cruise ship via satellite Internet


Contact Sylvestre on Twitter at @slybridges