Bootstrapped Digest with Ashley Baxter Transistor (https://transistor.fm) https://feeds.transistor.fm/bootstrapped-digest-with-ashley-baxter A transparent account of bootstrapping an insurance business as a solo founder. © Ashley Baxter 12f011ff-f735-5a96-ad11-36a2d0af3fbe yes en Tue, 24 Mar 2026 07:46:53 +0000 Tue, 24 Mar 2026 07:47:07 +0000 https://iamashley.co.uk https://img.transistorcdn.com/uFjOTqWhBbHuh4hjibubLjGPieMuSmSpo6SC6U6dMUE/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9zaG93/LzMzLzE2NTY1MTY3/NDUtYXJ0d29yay5q/cGc.jpg Bootstrapped Digest with Ashley Baxter https://iamashley.co.uk episodic Ashley Baxter A transparent account of bootstrapping an insurance business as a solo founder. A transparent account of bootstrapping an insurance business as a solo founder.. business, bootstrapping, marketing, startups, insurance Ashley Baxter No No Migrating ~ 1,400 customers to a new system without chaos. Here’s my plan 30 30 Migrating ~ 1,400 customers to a new system without chaos. Here’s my plan full 273a07f1-66a4-46e3-b3b9-6f6e12931568 https://share.transistor.fm/s/4a89249c
  • The road to automating my business
  • Vicky Gu
    • ]]>
  • The road to automating my business
  • Vicky Gu
    • ]]>     Tue, 24 Mar 2026 07:46:53 +0000 Ashley Baxter Ashley Baxter 1177
  • The road to automating my business
  • Vicky Gu
    • ]]>     business, bootstrapping, marketing, startups, insurance No     It's just a giant calculator 29 29 It's just a giant calculator full a251522f-c4a1-4402-b495-68ea78a60465 https://share.transistor.fm/s/a795fe29
  • My new system - tell your freelance friends?
  • The startups for the rest of us episode I was on
    • ]]>
  • My new system - tell your freelance friends?
  • The startups for the rest of us episode I was on
    • ]]>     Tue, 10 Mar 2026 12:51:49 +0000 Ashley Baxter Ashley Baxter 737
  • My new system - tell your freelance friends?
  • The startups for the rest of us episode I was on
    • ]]>     business, bootstrapping, marketing, startups, insurance No     Do things that don't scale 28 28 Do things that don't scale full 47090240-4669-44d2-94fd-7f18b408cf4b https://share.transistor.fm/s/f9fe977f
  • With Jack
  • I am Ashley
  • Paul Graham's essay, do things that don't scale
    • ]]>
  • With Jack
  • I am Ashley
  • Paul Graham's essay, do things that don't scale
    • ]]>     Mon, 15 Aug 2022 08:00:00 +0100 Ashley Baxter Ashley Baxter 744 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 process quotes, renewals, cancellations and everything in between. The automated quote and bind system is in development, but there are so many benefits of doing things that don’t scale. Let's talk about them. 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 process quotes, renewals, cancellations and everything in between. The auto business, bootstrapping, marketing, startups, insurance No     "This is so much bigger than me" 27 27 "This is so much bigger than me" full 15796138-0474-447a-b8d5-58613a678b94 https://share.transistor.fm/s/3c8d5b08
  • With Jack
  • I am Ashley
    • ]]>
  • With Jack
  • I am Ashley
    • ]]>     Mon, 18 Jul 2022 11:30:00 +0100 Ashley Baxter Ashley Baxter 761 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 date this has been a 2.5 year process and it hasn't been without its bumps in the road. I think I'm the first one-person business to go through this process and I feel so overwhelmed. 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 date this has been a 2.5 year process and it hasn't been without its bum business, bootstrapping, marketing, startups, insurance No     The road to automating my business 26 26 The road to automating my business full 8e2250cb-2d10-431d-8d55-70471081bbff https://share.transistor.fm/s/dd659d8b
  • With Jack
  • I am Ashley
    • ]]>
  • With Jack
  • I am Ashley
    • ]]>     Mon, 04 Jul 2022 08:00:00 +0100 Ashley Baxter Ashley Baxter 896 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. 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. business, bootstrapping, marketing, startups, insurance No     Product-market fit struggles 25 25 Product-market fit struggles full 3d4bc331-f6a7-422f-be5e-0f5f743f1b9e https://share.transistor.fm/s/3c5442f7
  • 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
    • ]]>
  • 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
    • ]]>     Mon, 15 Feb 2021 20:37:32 +0000 Ashley Baxter Ashley Baxter 958 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 definitions and talk about how With Jack measures up. 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 definitions and talk about how With Jack measures up. business, bootstrapping, marketing, startups, insurance No     This is not a year in review 24 24 This is not a year in review full f27375ad-d7cc-47a7-ad17-231805ada461 https://share.transistor.fm/s/480cecb8
  • 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
    • ]]>
  • 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
    • ]]>     Tue, 26 Jan 2021 21:52:39 +0000 Ashley Baxter Ashley Baxter 1291 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 year and the lessons I learned. We're still not out of the woods yet, but I now feel ready to talk about the impact the pandemic has had on my business. 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 year and the lessons I learned. We're still not out of the woods yet, but I business, bootstrapping, marketing, startups, insurance No     My mid-Year review 23 23 My mid-Year review full 0054e8bf-748e-4969-ad93-08aa9ce9e8af https://share.transistor.fm/s/26e4450a
  • Mid year review blog post
  • Reflecting on a disappointing product launch
  • SuperHi
  • Scott, the freelancer I work with 
  • Follow me on Twitter
    • ]]>
  • Mid year review blog post
  • Reflecting on a disappointing product launch
  • SuperHi
  • Scott, the freelancer I work with 
  • Follow me on Twitter
    • ]]>     Fri, 26 Jul 2019 13:35:00 +0100 Ashley Baxter Ashley Baxter 891 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? 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 evolve business, bootstrapping, marketing, startups, insurance No     Why can't I celebrate tiny wins? 22 22 Why can't I celebrate tiny wins? full a030b8cd-b909-4720-8150-98fc4033bec1 https://share.transistor.fm/s/879220af
  • With Jack
  • Why can't I celebrate tiny wins blog post
    • ]]>
  • With Jack
  • Why can't I celebrate tiny wins blog post
    • ]]>     Fri, 28 Jun 2019 10:40:00 +0100 Ashley Baxter Ashley Baxter 760 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. 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 achieve business, bootstrapping, marketing, startups, insurance No     Mistakes I made when choosing a market 21 21 Mistakes I made when choosing a market full 98aab446-09a8-4146-b8bb-515e07121709 https://share.transistor.fm/s/0015f6f3
  • Thoughts on choosing a market blog post
  • With Jack
  • Should you build a product for a user segment you're not a part of?
  • Five ways to build a $100 million business
  • Justin's Twitter thread about fishing
    • ]]>
  • Thoughts on choosing a market blog post
  • With Jack
  • Should you build a product for a user segment you're not a part of?
  • Five ways to build a $100 million business
  • Justin's Twitter thread about fishing
    • ]]>     Wed, 19 Jun 2019 17:20:00 +0100 Ashley Baxter Ashley Baxter 1071 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. 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 befo business, bootstrapping, marketing, startups, insurance No     Reflecting on a disappointing product launch 20 20 Reflecting on a disappointing product launch full 06036ebb-d3bd-4fb8-a77e-3c6d32567515 https://share.transistor.fm/s/6560a17a
  • Reflecting on a disappointing product launch blog post
  • Rome selfie while I'm on the phone to customers
  • My new product
  • A post-mortem on shutting down a product we just launched
    • ]]>
  • Reflecting on a disappointing product launch blog post
  • Rome selfie while I'm on the phone to customers
  • My new product
  • A post-mortem on shutting down a product we just launched
    • ]]>     Thu, 11 Apr 2019 10:30:00 +0100 Ashley Baxter Ashley Baxter 921 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. 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 s business, bootstrapping, marketing, startups, insurance No     The challenges of building an insurance business 19 19 The challenges of building an insurance business full a85e6289-1902-41ff-a8e3-2d7f498de5f3 https://share.transistor.fm/s/f0bf538f
  • The challenges of building an insurance business blog post
  • Kinsu
  • The Digital Insurer
  • With Jack
  • World's only public benefit insurance company, Lemonade
  • My photography business
    • ]]>
  • The challenges of building an insurance business blog post
  • Kinsu
  • The Digital Insurer
  • With Jack
  • World's only public benefit insurance company, Lemonade
  • My photography business
    • ]]>     Wed, 27 Mar 2019 14:00:00 +0000 Ashley Baxter Ashley Baxter 757 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. 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 g business, bootstrapping, marketing, startups, insurance No     Lessons learned from inheriting the family business 18 18 Lessons learned from inheriting the family business full 2fb03284-fd3d-458d-a297-e957f56e4ce5 https://share.transistor.fm/s/921f258f
  • Before UpFront
  • The family business
  • With Jack
    • ]]>
  • Before UpFront
  • The family business
  • With Jack
    • ]]>     Thu, 14 Mar 2019 14:10:00 +0000 Ashley Baxter Ashley Baxter 762 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. 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 upsid business, bootstrapping, marketing, startups, insurance No     Should you build a product for a user segment you're not a part of? 17 17 Should you build a product for a user segment you're not a part of? full cab7a66d-ea94-4fe4-aeeb-bd268680acc2 https://share.transistor.fm/s/c814f6b7
  • Should you build a product for a user segment you're not a part of blog post
  • The family business
  • With Jack's new product, legal expenses
  • @iamashley on Twitter
    • ]]>
  • Should you build a product for a user segment you're not a part of blog post
  • The family business
  • With Jack's new product, legal expenses
  • @iamashley on Twitter
    • ]]>     Wed, 06 Mar 2019 18:00:00 +0000 Ashley Baxter Ashley Baxter 771 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). 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 business, bootstrapping, marketing, startups, insurance No     How has the rebrand performed 4 months on? 16 16 How has the rebrand performed 4 months on? full 5932ecb0-a5bd-4d81-8c96-0af5fabf1f11 https://share.transistor.fm/s/23a25ad0
  • How has the rebrand performed 4 months on? blog post
  • With Jack
  • The processes and reasons behind With Jack's rebrand
  • My newsletter!
    • ]]>
  • How has the rebrand performed 4 months on? blog post
  • With Jack
  • The processes and reasons behind With Jack's rebrand
  • My newsletter!
    • ]]>     Mon, 25 Feb 2019 18:30:00 +0000 Ashley Baxter Ashley Baxter 576 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. 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 business, bootstrapping, marketing, startups, insurance No     Company/founder fit 15 15 Company/founder fit full 53e572db-b2db-4c25-84e0-fec47de9ea4f https://share.transistor.fm/s/11d3fb6c
  • Company/founder fit blog post
  • With Jack
  • You want more than product/market fit
  • Will it fly?
  • My freelance photography blog
  • Patreon, venture capital and the loss of the win-win
    • ]]>
  • Company/founder fit blog post
  • With Jack
  • You want more than product/market fit
  • Will it fly?
  • My freelance photography blog
  • Patreon, venture capital and the loss of the win-win
    • ]]>     Mon, 18 Feb 2019 13:30:00 +0000 Ashley Baxter Ashley Baxter 593 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. 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 rea business, bootstrapping, marketing, startups, insurance No     In the trench tips for figuring out what problem you solve 14 14 In the trench tips for figuring out what problem you solve full fe583484-b057-4014-8387-18182a7f38b7 https://share.transistor.fm/s/99ec2e7d
  • In the trench tips for figuring out what problem you solve blog post
  • With Jack
  • The Ultimate List of Customer Development Questions
  • Ignite
  • From Scratch
  • My Twitter
    • ]]>
  • In the trench tips for figuring out what problem you solve blog post
  • With Jack
  • The Ultimate List of Customer Development Questions
  • Ignite
  • From Scratch
  • My Twitter
    • ]]>     Tue, 12 Feb 2019 11:40:00 +0000 Ashley Baxter Ashley Baxter 936 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. 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 wh business, bootstrapping, marketing, startups, insurance No     2018: Year in review 13 13 2018: Year in review full ecf31e77-5608-46dd-a593-fcf0f3d89dd8 https://share.transistor.fm/s/4c533f1c
  • 2018: Year in review blog post
  • With Jack
  • With Jack's YouTube channel
  • With Jack is now authorised by the FCA blog post
  • My trip to Lanzarote
  • My trip to Amsterdam
  • My trip to California
  • My trip to Dubrovnik
    • ]]>
  • 2018: Year in review blog post
  • With Jack
  • With Jack's YouTube channel
  • With Jack is now authorised by the FCA blog post
  • My trip to Lanzarote
  • My trip to Amsterdam
  • My trip to California
  • My trip to Dubrovnik
    • ]]>     Mon, 17 Dec 2018 10:30:00 +0000 Ashley Baxter Ashley Baxter 1129 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. 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 business, bootstrapping, marketing, startups, insurance No     How to start scrappy in a regulated industry 12 12 How to start scrappy in a regulated industry full 93b5526b-2abe-4bdf-a5bf-4ed5d9b69c0d https://share.transistor.fm/s/5e839e28
  • How to start scrappy in a regulated industry blog post
  • With Jack
    • ]]>
  • How to start scrappy in a regulated industry blog post
  • With Jack
    • ]]>     Tue, 04 Dec 2018 09:40:00 +0000 Ashley Baxter Ashley Baxter 884 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? 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 c business, bootstrapping, marketing, startups, insurance No     Post-launch problems revisited 11 11 Post-launch problems revisited full b11ddf58-4322-424f-ab7f-7654b6a9551c https://share.transistor.fm/s/27f03caa
  • Post-launch problems revisited blog post
  • Navigating a funk as a solo founder blog post
  • With Jack
    • ]]>
  • Post-launch problems revisited blog post
  • Navigating a funk as a solo founder blog post
  • With Jack
    • ]]>     Thu, 29 Nov 2018 11:30:00 +0000 Ashley Baxter Ashley Baxter 735 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. 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. business, bootstrapping, marketing, startups, insurance No     The process and reasons behind With Jack's rebrand 10 10 The process and reasons behind With Jack's rebrand full 14f375eb-e9b6-4485-b93f-3fde7b6dd186 https://share.transistor.fm/s/f0313cde

    ]]>

    ]]>     Thu, 08 Nov 2018 14:00:00 +0000 Ashley Baxter Ashley Baxter 1035 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… 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… business, bootstrapping, marketing, startups, insurance No     Navigating a funk as a solo founder 9 9 Navigating a funk as a solo founder full 02f838f9-7e1a-4988-8b47-5853bc75b873 https://share.transistor.fm/s/1aed6ea8
  • Navigating a funk as a solo founder
  • With Jack
  • Epicurrence
  • Tweet about momentum
  • Tweet about being in a funk
    • ]]>
  • Navigating a funk as a solo founder
  • With Jack
  • Epicurrence
  • Tweet about momentum
  • Tweet about being in a funk
    • ]]>     Fri, 07 Sep 2018 10:40:00 +0100 Ashley Baxter Ashley Baxter 587 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 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. business, bootstrapping, marketing, startups, insurance No     Why I quit wedding photography 8 8 Why I quit wedding photography full 5b182751-01a1-4178-929a-a86581aba08a https://share.transistor.fm/s/ce965955
  • Why I quit wedding photography
  • With Jack
  • My photography
    • ]]>
  • Why I quit wedding photography
  • With Jack
  • My photography
    • ]]>     Thu, 23 Aug 2018 13:35:00 +0100 Ashley Baxter Ashley Baxter 474 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'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 business, bootstrapping, marketing, startups, insurance No     Positioning your product to a tiny audience 7 7 Positioning your product to a tiny audience full d29a4cc3-f4b8-4f0e-8894-cedabf1d2524 https://share.transistor.fm/s/b6fc77a8
  • Positioning your product to a tiny audience blog post
  • How Seth Godin Would Launch A New Business
  • With Jack
  • Justin Jackson's article on founder / market fit
  • SaaS pricing advice (Build Your SaaS podcast)
    • ]]>
  • Positioning your product to a tiny audience blog post
  • How Seth Godin Would Launch A New Business
  • With Jack
  • Justin Jackson's article on founder / market fit
  • SaaS pricing advice (Build Your SaaS podcast)
    • ]]>     Mon, 11 Jun 2018 14:30:00 +0100 Ashley Baxter Ashley Baxter 1023 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. 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 produ business, bootstrapping, marketing, startups, insurance No     Bootstrapping Niice to 100,000 users 6 6 Bootstrapping Niice to 100,000 users full 79ed8239-feb4-44f9-9bfd-57be7568e3af https://share.transistor.fm/s/980b92d2
  • Niice
  • Chris on Twitter
    • ]]>
  • Niice
  • Chris on Twitter
    • ]]>     Wed, 30 May 2018 15:30:00 +0100 Ashley Baxter Ashley Baxter 3822 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. 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 l business, bootstrapping, marketing, startups, insurance No     Start talking about your idea 5 5 Start talking about your idea full 06e9344e-0283-48e1-927e-e747fe70d6fa https://share.transistor.fm/s/2d1e50f0
  • Start talking about your idea
  • With Jack
  • Idea to Execution and Beyond
  • Masters of Scale—How to price your product to scale
    • ]]>
  • Start talking about your idea
  • With Jack
  • Idea to Execution and Beyond
  • Masters of Scale—How to price your product to scale
    • ]]>     Thu, 17 May 2018 13:30:00 +0100 Ashley Baxter Ashley Baxter 1282 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. 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 business, bootstrapping, marketing, startups, insurance No     My journey to 250 customers 4 4 My journey to 250 customers full 51ee98bc-2fd7-4fa7-af7a-4308ad87309c https://share.transistor.fm/s/1d283c7b
  • Notist
  • My journey to 250 customers
    • ]]>
  • Notist
  • My journey to 250 customers
    • ]]>     Tue, 08 May 2018 11:45:00 +0100 Ashley Baxter Ashley Baxter 937 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. 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 business, bootstrapping, marketing, startups, insurance No     The 'why' behind building With Jack 3 3 The 'why' behind building With Jack full 1d319c10-d9be-420c-8c98-884629770249 https://share.transistor.fm/s/48f42147
  • The 'Why' Behind Building With Jack blog post
  • My YouTube channel
  • Everybody's Winging It by Baremetrics
  • Toad's Caravan
    • ]]>
  • The 'Why' Behind Building With Jack blog post
  • My YouTube channel
  • Everybody's Winging It by Baremetrics
  • Toad's Caravan
    • ]]>     Tue, 17 Apr 2018 16:20:00 +0100 Ashley Baxter Ashley Baxter 1107 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. 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 Bootstrapping, Business, Insurtech No     How I improved With Jack's sign-up rate by 14% 2 2 How I improved With Jack's sign-up rate by 14% full 7b2f4800-ffb7-42c3-85fa-f1ad25c7fafa https://share.transistor.fm/s/41b59ef4
  • All Day Hey!
  • Improving With Jack's Sign-Up Rate By 14%
  • Naomi Atkinson Design
  • Scott Riley
    • ]]>
  • All Day Hey!
  • Improving With Jack's Sign-Up Rate By 14%
  • Naomi Atkinson Design
  • Scott Riley
    • ]]>     Thu, 22 Mar 2018 14:00:00 +0000 Ashley Baxter Ashley Baxter 680 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 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%. Business, Insurance, Bootstrapping, Sales No     Minimum viable process 1 1 Minimum viable process full 96280930-652a-438d-934f-6f07f9a68c92 https://share.transistor.fm/s/ad5adb01 Links

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    ]]>     Wed, 14 Mar 2018 17:00:00 +0000 Ashley Baxter Ashley Baxter 1086 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. 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 me business, bootstrapping, startup, insurance No