Episodes

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Do things that don't scale

Do things that don't scale

Episode 28 · · 12:24

In Paul Graham’s essay, do things that don’t scale, he talks about you acting as the software, doing things manually that you plan to automate later. Currently I’m the software. I pr...

"This is so much bigger than me"

"This is so much bigger than me"

Episode 27 · · 12:41

Following on from the last episode where I talked about why now is the right time to automate the business, in this episode I go into more detail about what’s required to do that. To...

The road to automating my business

The road to automating my business

Episode 26 · · 14:56

I've been MIA but this episode will explain why. This is the long, hard road to automating my business—a process that I'm 2.5 years (and counting!) into.

Product-market fit struggles

Product-market fit struggles

Episode 25 · · 15:58

Despite being 4 years into building With Jack I'm not convinced I have product-market fit. Everyone has a different definition of what PMF is, so I go through some of the popular def...

This is not a year in review

This is not a year in review

Episode 24 · · 21:31

I'm back with a long overdue update! In this episode I document what it was like bootstrapping my business through a pandemic as a solo founder. I share the challenges of the past ye...

My mid-Year review

My mid-Year review

Episode 23 · · 14:51

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 r...

Why can't I celebrate tiny wins?

Why can't I celebrate tiny wins?

Episode 22 · · 12:40

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 shoc...

Mistakes I made when choosing a market

Mistakes I made when choosing a market

Episode 21 · · 17:51

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 s...

Reflecting on a disappointing product launch

Reflecting on a disappointing product launch

Episode 20 · · 15:21

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 under...

The challenges of building an insurance business

The challenges of building an insurance business

Episode 19 · · 12:37

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 ...

Lessons learned from inheriting the family business

Lessons learned from inheriting the family business

Episode 18 · · 12:42

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 ab...

Should you build a product for a user segment you're not a part of?

Should you build a product for a user segment you're not a part of?

Episode 17 · · 12:51

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 befor...

How has the rebrand performed 4 months on?

How has the rebrand performed 4 months on?

Episode 16 · · 09:36

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 webs...

Company/founder fit

Company/founder fit

Episode 15 · · 09:53

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...

In the trench tips for figuring out what problem you solve

In the trench tips for figuring out what problem you solve

Episode 14 · · 15:36

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 e...

2018: Year in review

2018: Year in review

Episode 13 · · 18:49

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,...

How to start scrappy in a regulated industry

How to start scrappy in a regulated industry

Episode 12 · · 14:44

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 t...

Post-launch problems revisited

Post-launch problems revisited

Episode 11 · · 12:15

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 seco...

The process and reasons behind With Jack's rebrand

The process and reasons behind With Jack's rebrand

Episode 10 · · 17:15

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

Navigating a funk as a solo founder

Episode 9 · · 09:47

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 abo...

Why I quit wedding photography

Why I quit wedding photography

Episode 8 · · 07:54

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 a...

Positioning your product to a tiny audience

Positioning your product to a tiny audience

Episode 7 · · 17:03

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 ...

Bootstrapping Niice to 100,000 users

Bootstrapping Niice to 100,000 users

Episode 6 · · 01:03:42

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 ...

Start talking about your idea

Start talking about your idea

Episode 5 · · 21:22

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...

My journey to 250 customers

My journey to 250 customers

Episode 4 · · 15:37

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 im...

The 'why' behind building With Jack

The 'why' behind building With Jack

Episode 3 · · 18:27

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 ...

How I improved With Jack's sign-up rate by 14%

How I improved With Jack's sign-up rate by 14%

Episode 2 · · 11:20

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

Minimum viable process

Episode 1 · · 18:06

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...