Bootstrapped Digest with Ashley Baxter
By Ashley Baxter
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A transparent account of bootstrapping an insurance business as a solo founder.
||CleanHow to start scrappy in a regulated industry||Insurance is one of the least start-up friendly industries in the world. It's a regulated industry, so you can't just have an idea, buy a domain and start making money. You'll need to be licensed to sell insurance, and that takes between 6-12 months and||12/4/2018||Free||View in iTunes|
||CleanPost-launch problems revisited||In this episode I revisit some of the problems I faced post-launch. I talk about what I've learned, if I've solved those problems and some of the new challenges I'm facing in my second year in business.||11/29/2018||Free||View in iTunes|
||CleanThe Process and Reasons Behind With Jack's Rebrand||With Jack has a brand new look! I dive into the reasons behind the redesign, the process and what we tried to achieve. As always, I also share some things that didn't go to plan…||11/8/2018||Free||View in iTunes|
||CleanNavigating a funk as a solo founder||I've been feeling in a bit of a funk lately. It's a dangerous place to be as a solo founder because there's nobody to pick up the slack so you can recharge your batteries. I talk about identifying what triggered my funk and how I got out of it.||9/7/2018||Free||View in iTunes|
||CleanWhy I quit wedding photography||I've finished shooting my last wedding ever! I talk about some of the factors that influenced my decision to quit wedding photography. Wedding photography helped me fund the design and development costs of building With Jack, but it's time to say good b||8/23/2018||Free||View in iTunes|
||CleanPositioning Your Product to a Tiny Audience||I talk about the importance of positioning. From my early days where I didn't know or specify who my product was for, to now where I'm laser focused on a small group of people. This allows me to focus my messaging, marketing, customer experience and pro||6/11/2018||Free||View in iTunes|
||CleanBootstrapping Niice to 100,000 users||In this episode I speak to Chris Armstrong, designer and founder. Chris started Niice as a side project 5 years ago. It's now a SaaS app with 100K+ users. We talk about launching at 2.30 in the morning, how he figured out who his target audience was and||5/30/2018||Free||View in iTunes|
||CleanStart talking about your idea||I used to dive straight into my code editor without talking to potential customers. This lead to a lot of failed projects. Today I share two experiences. One where I built my project in secrecy and kept my cards close to my chest. The other project wher||5/17/2018||Free||View in iTunes|
||CleanMy journey to 250 customers||How has the journey to 250 customers looked for me? In a world where TechCrunch articles celebrate the overnight success story, I share my journey of slow and organic growth. It's important we remember growth doesn't look the same for everyone, therefor||5/8/2018||Free||View in iTunes|
||CleanThe 'why' behind building With Jack||It's been a stressful few weeks, but I got through it thanks to a post-it note from 2013 reminding me why I started this business. In this episode, I share the rollercoaster ride of building a start-up. I talk about my original mission with building Wit||4/17/2018||Free||View in iTunes|
||CleanHow I improved With Jack's sign-up rate by 14%||I talk through the tweaks we made to the customer journey that lead to a 14% increase in sign-ups. These are simple and quick wins that took With Jack's conversion rate from 26% to 40%.||3/22/2018||Free||View in iTunes|
||CleanMinimum viable process||I launched an insurance company in 2016 without instant quotes. For the past 200+ sales I've been manually processing everything. In today's episode I make the argument for launching with the simplest version of your product or service, which sometimes||3/14/2018||Free||View in iTunes|