Bootstrapped Digest with Ashley Baxter

With Jack I am Ashley Paul Graham's essay, do things that don't scale

With Jack I am Ashley

With Jack I am Ashley

Product-market fit struggles blog post With Jack Lenny's newsletter How to know if you've got product-market fit Reflecting on a disappointing product launch Lemonade's IPO breakdown

This is not a year in review blog post 'Why do I need insurance?' guide The Jobs To Be Done Playbook My film photography My Twitter

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 evolved into something new, or have I shelved them completely?

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 achievement sink in. In this episode I talk about why I’m finding it difficult to celebrate my tiny wins.

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 beforehand. If you’re starting a business you will want to consider these factors, too.

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 share what I learned.

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 go out of business after a year. Here are some of my thoughts on the challenges of building an insurance business.

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 upside is coming away from that experience having learned a lot. In this episode I share some of the lessons I learned and how I’m applying them to With Jack so I can avoid making the same mistakes.

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 share my experience on both sides and my argument for building a product for a user segment you’re a part of (or familiar with).

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 the rebrand has performed and share a few lessons learned.

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 read Pat Flynn's book, 'Will It Fly?'. I share the exercise from 'Will It Fly?' that helped me get clarity on what's important to me in life and figure out what company/founder fit means to me.

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 what problem With Jack does solve, but from a pain-point customer driven perspective.

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 Jack.

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 costs thousands of pounds. For those of us who don't want to raise, how can you quickly and cheaply get started in insurance?

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.

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…

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.

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 to that part of my life.

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 products. This episode is all about the power of positioning.

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 learning how to talk about his product in a way that would appeal to them.

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 I started small, built in public and talked to my customers. It's no coincidence the latter is the project that's made money from day one. All of this leads to me sharing why I think it's important you talk about your idea.

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 we must not give up if we fail to hit 6 digits in 48 hours.

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 Jack and if—1.5 years into launch—I've managed to achieve it.

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%.

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 mean manual processes.