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2018: Year in review

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.

How to start scrappy in a regulated industry

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?

Post-launch problems revisited

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

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

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

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.

Positioning Your Product to a Tiny Audience

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.

Bootstrapping Niice to 100,000 users

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.

Start talking about your idea

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.

My journey to 250 customers

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.

The 'why' behind building With Jack

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.

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

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

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.

© Ashley Baxter