Bootstrapped Digest with Ashley Baxter

Bootstrapped Digest with Ashley Baxter
A transparent account of bootstrapping an insurance business as a solo founder..
Company/founder fit
Feb 18 • 9 min
To take investment or not? It’s a question I’ve struggled with since launching With Jack. The answer hinges on what kind of life I want to lead, therefore what kind of company I want to build. That was another question I’ve struggled to answer until I…
In the trench tips for figuring out what problem you solve
Feb 12 • 15 min
In 2017 I applied to join an accelerator. Amongst all of the great advice I received from the programme, I kept hearing the same feedback about With Jack; “You aren’t solving a big enough problem”. In this episode I share the steps I took to figure out…
2018: Year in review
Dec 17, 2018 • 18 min
It’s time to look back on 2018! The highs, the lows and notable moments. Two things stand out to me about 2018: the progress I’ve made on With Jack and the trips I’ve taken. However, it hasn’t all been great. I also share some end-of-year figures for With…
How to start scrappy in a regulated industry
Dec 4, 2018 • 14 min
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…
Post-launch problems revisited
Nov 29, 2018 • 12 min
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.
The Process and Reasons Behind With Jack’s Rebrand
Nov 8, 2018 • 17 min
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…
Navigating a funk as a solo founder
Sep 7, 2018 • 9 min
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.
Why I quit wedding photography
Aug 23, 2018 • 7 min
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 bye…
Positioning Your Product to a Tiny Audience
Jun 11, 2018 • 17 min
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…
Bootstrapping Niice to 100,000 users
May 30, 2018 • 63 min
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…
Start talking about your idea
May 17, 2018 • 21 min
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 where…
My journey to 250 customers
May 8, 2018 • 15 min
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, therefore…
The ‘why’ behind building With Jack
Apr 17, 2018 • 18 min
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 With…
How I improved With Jack’s sign-up rate by 14%
Mar 22, 2018 • 11 min
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%.
Minimum viable process
Mar 14, 2018 • 18 min
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…