Episode 30 · · 19:37
The road to automating my businessVicky Gu
Episode 29 · · 12:17
My new system - tell your freelance friends?The startups for the rest of us episode I was on
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...
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...
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.
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...
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...
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...
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...
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...
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...
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 ...
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...
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...
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...
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...
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...
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,...
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...
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...