Product-market fit struggles blog postWith JackLenny's newsletterHow to know if you've got product-market fitReflecting on a disappointing product launchLemonade's IPO breakdown

This is not a year in review

Jan 26th, 2021 21m 31s

This is not a year in review blog post'Why do I need insurance?' guideThe Jobs To Be Done PlaybookMy film photographyMy Twitter

My mid-Year review

Jul 26th, 2019 14m 51s

Mid year review blog postReflecting on a disappointing product launchSuperHiScott, the freelancer I work with Follow me on Twitter

Why can't I celebrate tiny wins?

Jun 28th, 2019 12m 40s

With JackWhy can't I celebrate tiny wins blog post

Mistakes I made when choosing a market

Jun 19th, 2019 17m 51s

Thoughts on choosing a market blog postWith JackShould you build a product for a user segment you're not a part of?Five ways to build a $100 million businessJustin's Twitter thread about fishing

Reflecting on a disappointing product launch

Apr 11th, 2019 15m 21s

Reflecting on a disappointing product launch blog postRome selfie while I'm on the phone to customersMy new productA post-mortem on shutting down a product we just launched

The challenges of building an insurance business

Mar 27th, 2019 12m 37s

The challenges of building an insurance business blog postKinsuThe Digital InsurerWith JackWorld's only public benefit insurance company, LemonadeMy photography business

Lessons learned from inheriting the family business

Mar 14th, 2019 12m 42s

Before UpFrontThe family businessWith Jack

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

Mar 6th, 2019 12m 51s

Should you build a product for a user segment you're not a part of blog postThe family businessWith Jack's new product, legal expenses@iamashley on Twitter

How has the rebrand performed 4 months on?

Feb 25th, 2019 9m 36s

How has the rebrand performed 4 months on? blog postWith JackThe processes and reasons behind With Jack's rebrandMy newsletter!

Company/founder fit

Feb 18th, 2019 9m 53s

Company/founder fit blog postWith JackYou want more than product/market fitWill it fly?My freelance photography blogPatreon, venture capital and the loss of the win-win

In the trench tips for figuring out what problem you solve

Feb 12th, 2019 15m 36s

In the trench tips for figuring out what problem you solve blog postWith JackThe Ultimate List of Customer Development QuestionsIgniteFrom ScratchMy Twitter

2018: Year in review

Dec 17th, 2018 18m 49s

2018: Year in review blog postWith JackWith Jack's YouTube channelWith Jack is now authorised by the FCA blog postMy trip to LanzaroteMy trip to AmsterdamMy trip to CaliforniaMy trip to Dubrovnik

How to start scrappy in a regulated industry

Dec 4th, 2018 14m 44s

How to start scrappy in a regulated industry blog postWith Jack

Post-launch problems revisited

Nov 29th, 2018 12m 15s

Post-launch problems revisited blog postNavigating a funk as a solo founder blog postWith Jack

The process and reasons behind With Jack's rebrand

Nov 8th, 2018 17m 15s

The Process and Reasons Behind With Jack's Redesign blog postWith JackSabine's case studyVic Bell's DribbbleScott's website

Navigating a funk as a solo founder

Sep 7th, 2018 9m 47s

Navigating a funk as a solo founderWith JackEpicurrenceTweet about momentumTweet about being in a funk

Why I quit wedding photography

Aug 23rd, 2018 7m 54s

Why I quit wedding photographyWith JackMy photography

Positioning your product to a tiny audience

Jun 11th, 2018 17m 3s

Positioning your product to a tiny audience blog postHow Seth Godin Would Launch A New BusinessWith JackJustin Jackson's article on founder / market fitSaaS pricing advice (Build Your SaaS podcast)