Bootstrapped Digest with Ashley Baxter

Bootstrapped Digest with Ashley Baxter
A transparent account of bootstrapping an insurance business as a solo founder..

My mid-Year review
Jul 26, 2019 • 14 min
We’re 55% of the way through 2019! Coupled with the start of summer being quieter for my business, now seems a good time to revisit some of the goals I set myself and do a mid-year review. How am I doing? Am I on my way to achieving them, have they…
Why can’t I celebrate tiny wins?
Jun 28, 2019 • 12 min
Last week With Jack hit a huge milestone. Despite this being something I have been working towards for so long, I didn’t feel anything when it happened. My friends said I was in shock. Over a week has passed and I’ve had plenty of time to let this…
Mistakes I made when choosing a market
Jun 19, 2019 • 17 min
Before starting my business I hadn’t given much thought to what goes into choosing a good market. I love targeting freelancers, but that doesn’t mean I’ve chosen an ideal market to sell to and I want to share some of the factors I wish I’d considered…
Reflecting on a disappointing product launch
Apr 11, 2019 • 15 min
In March I launched a new product. I was excited about this product because it has a myriad of features that solve problems freelancers face regularly. The launch, however, was underwhelming. In this episode I dissect my disappointing product launch and…
The challenges of building an insurance business
Mar 27, 2019 • 12 min
Another UK insurtech has closed its doors. Insurtech or not, VC-funded or not, building a business in the insurance space is a lot tougher than all us ‘disruptors’ anticipate. We’re seeing insurtechs challenge the status quo and execute beautifully, yet…
Lessons learned from inheriting the family business
Mar 14, 2019 • 12 min
In 2005 I inherited an insurance business from my late Dad. Weeks earlier I had been studying music at college. It was big leap to running a business in an industry I knew nothing about. Trying something new inevitably means making mistakes, but the…
Should you build a product for a user segment you’re not a part of?
Mar 6, 2019 • 12 min
A podcast listener emailed me the question, “Would you build a product for a user segment that you’re not a part of?”. I’ve built a product for an audience I knew nothing about before moving into a user segment I’m more familiar with. In today’s episode I…
How has the rebrand performed 4 months on?
Feb 25, 2019 • 9 min
4 months ago we shipped a major update to With Jack. A brand new look plus instant quotes! Once the post-launch dust had settled there was one niggling fear I had… Will this new website still make money? In this episode I dive into the numbers to see how…
Company/founder fit
Feb 18, 2019 • 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, 2019 • 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…