Episode 597 | The Challenge of Building a Business in a Regulated Industry

Startups For the Rest of Us

Rob Walling

Management, Entrepreneurship, Business, Marketing

4.8 • 792 Ratings

🗓️ 5 April 2022

⏱️ 37 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

In episode 597, Rob Walling chats with Ashley Baxter, the founder of With Jack. With Jack gives peace of mind and protection for UK freelancers through insurance, professional indemnity, public liability, contracts, legal expenses, etc. We dig into the lessons Ashley learned from a failed insurance business she inherited from her father, how she used her freelance photography to fund With Jack in the early days, along with sharing many of the successes and failures she has had on her entrepreneurial journey. Topics we cover: [1:49] Tickets for MicroConf Remote 4.0 are now on sale [2:55] Putting a tech twist on a regulated industry [3:27] Improving the onboarding experience [5:24] How Ashley came up with the name for her business, With Jack [8:24] How she used the money from her freelance photography business to fund the early development costs for With Jack [10:16] Lessons learned from taking over her father’s insurance business at 18 [15:20] The danger of depending on only one channel to run your business [17:49] Ashley’s three pivotal business moments [21:27] The concept of a vitamin vs. painkiller business [27:10] The challenges of hiring an executive or admin assistant in a highly regulated industry [28:42] How Ashley responded when a competitor stole her website design [31:17] Why you shouldn’t be intimidated if a competitor gets funding Links from the Show: Ashley Baxter @iamashley I Twitter With Jack I Company Website Ashley Baxter I Ashley’s website If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you. Subscribe & Review: iTunes | Spotify | Stitcher

Transcript

Click on a timestamp to play from that location

0:00.0	He passed away when I was 18 and because I was the only person in the family with some experience
0:05.2	building websites and deploying them because I'd done so for a bunch of bands that I'd played in,
0:11.5	it kind of fell on me to keep my dad's business going. And whilst I was never able to make a success
0:17.3	of his business, I wanted to take everything that I'd learned from that and put
0:21.6	it into my own thing. When I was coming up with a name, I'm terrible at naming things actually,
0:26.9	but I knew that I wanted it to have a nod back to my dad. And so in the end, I just ended up
0:32.1	naming it after him. And the character that you see on the website, that is, of course, based on my dad.
0:44.2	Yeah. the character that you see on the website that is, of course, based on my dad. Welcome back to Startup for the rest of us. This is episode 597. We are approaching that 600
0:50.4	episode mark. In today's episode of the show, I talk with Ashley Baxter. She's the founder of
0:56.2	WithJack, which is located on the interwebs at withjack.com.uk. And their H-1 is be a confident
1:03.7	freelancer. So With Jack gives peace of mind and protection for UK freelancers through insurance,
1:09.5	professional indemnity, public liability, contents,
1:12.2	legal expenses, etc. And today, Ashley and I dig into her pretty incredible story about
1:18.4	losing her father. She was relatively young and she took over his insurance business and it failed.
1:24.5	It didn't work out. But how she bounced back started with Jack and the successes and the failures, trials, and tribulations that have happened since then.
1:32.8	It's been a pretty incredible journey.
1:34.7	And she actually spoke about it at MicroConf Europe.
1:37.4	I believe it was in 2019.
1:39.6	So almost three years ago.
1:41.6	And she's come so far since then.
1:45.5	And, you know, he's really pushing,
1:49.8	still pushing the boulder up the hill and making progress. But before we dive into that,
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from Rob Walling, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Rob Walling and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.