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.

[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 

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.

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