Building a bootstrapped insurance business for freelancers in a regulated market

Executive overview

Ashley Baxter founded With Jack, a UK insurance brokerage for freelancers, after inheriting her late father's insurance affiliate business at 18 and watching it fail. The regulated nature of insurance creates compounding challenges: manual admin consumes founder time, market education is required before any sale, and the product is a vitamin not an aspirin.

The path forward is delegated authority — permission from insurers to quote and bind policies directly — which unlocks product creation and automation that frees time for higher-value work.

Insurance for freelancers is not a distribution problem; it is a market education and product-fit problem.

Origin and early failure

• Father ran a successful landlord insurance affiliate business built on strong Google SEO
• He passed away when Ashley was 18; she stepped in with website skills but no insurance knowledge
• Two simultaneous shocks destroyed the business: comparison sites drew traffic away from Google, and a Google algorithm update penalised keyword stuffing, delisting the sites entirely
• Core lesson: never depend on a single acquisition channel
• Rather than leaving insurance, Ashley saw the industry's poor design and tech as an opportunity worth exploring

Why insurance for freelancers

• Mainstream providers sell to everyone (estate agents, accountants, freelancers) — products are generic and poorly matched
• With Jack is laser-focused on creative freelancers, so customers get exactly the products they need
• Early goal was improving the onboarding and quote experience; that goal evolved
• Realisation: nobody walks around wanting to shave 60 seconds off buying insurance — slick UX alone is not a real problem to solve
• The real job: help freelancers feel confident enough to take on clients, handle disputes, and pursue their work without anxiety
• Only 5% of customers ever make a claim — the product's value for the other 95% is emotional and aspirational, not practical

The vitamin problem

• Insurance is a vitamin: people know they should have it, but lack urgency to act
• Roughly 75% of the estimated 2 million UK freelancers are uninsured
• Growth is slow not because the product is bad, but because the market requires education before conversion
• Funded insure-techs entering the space face the same slow-burn dynamic; VC timelines conflict with insurance growth rates
• Ashley has watched multiple funded competitors launch, struggle to gain traction, and sell or shut down

Manual admin as a growth ceiling

• Without delegated authority, Ashley manually processes quotes, renewals, midterm adjustments, and cancellations
• This consumes the time and mental bandwidth needed to develop new products and find the missing piece of the puzzle
• Delegated authority from insurers will allow her to build technology that handles these tasks automatically
• It will also allow her to design and sell her own insurance products, rather than just distributing others'
• Hiring a part-time admin assistant is a near-term stopgap; resistance to delegation is a common founder trap

Competing as a bootstrapped solo founder

• A funded competitor launched with a similar design, same insurer, same target demographic, and had tried to pick Ashley's brain years earlier
• The funding initially felt like a death sentence for With Jack
• Outcome: the competitor sold in a fire sale; a second similar startup also failed
• Bootstrapped founders often fear funded competitors more than warranted — capital without domain expertise does not compound the way experience does
• A bootstrapped founder who is capital-efficient and close to customers outlasts undifferentiated funded entrants in slow-growth regulated markets
• Ashley now treats new entrants as confirmation she identified a real market, not as existential threats

Where With Jack stands

• Fully self-sustaining; approaching £1 million in written premium
• First part-time hire recently onboarded
• Growth is consistent but slower than Ashley believes the effort invested warrants
• The missing piece — a product or service that serves the 95% of freelancers whose insurance never triggers — remains unsolved
• Target: 10,000 customers, a number she sees as manageable and sufficient to sustain the business on her terms