With Jack
Ashley Baxter's journey to founding With Jack was shaped by an unexpected inheritance. At just 18 years old, she took over her father's insurance business—a move that would teach her hard lessons about entrepreneurship, regulation, and business sustainability. Though that venture ultimately failed, the experience gave her deep insight into the insurance industry's pain points and the specific needs of UK freelancers seeking protection.
Rather than jumping directly into With Jack, Ashley used her freelance photography business to bootstrap the early development costs. This strategic decision allowed her to maintain financial independence while building the insurance platform without external pressure or investor constraints. She focused on putting a tech twist on the regulated insurance industry, emphasizing an improved onboarding experience to make insurance more accessible to independent workers.
Ashley's path to customers drew from her understanding of the freelancer pain point she experienced personally. By combining her knowledge from the failed insurance business with her credibility as a working freelancer, she was able to connect with early adopters who understood the value proposition immediately.
Ashley identified three pivotal business moments that shaped With Jack's trajectory. One critical lesson was the danger of depending on only one channel to run a business—a vulnerability that could threaten sustainability. When a competitor stole her website design, she responded with confidence rather than intimidation, reinforcing the principle that competitive threats, even when brazen, shouldn't derail vision execution. She also learned to reframe the market opportunity: distinguishing between a "vitamin" business (nice-to-have) and a "painkiller" business (essential). For freelancers facing real liability risks, With Jack positioned itself as a painkiller.
One operational challenge emerged when trying to hire an executive or administrative assistant in a highly regulated industry—the specialized knowledge required made hiring more complex than in typical SaaS businesses.
With Jack has established itself as a trusted insurance platform for UK freelancers, combining regulatory compliance with user-friendly technology. Ashley's willingness to share both successes and failures publicly demonstrates a mature approach to entrepreneurship and continues to attract freelancers seeking straightforward, tech-enabled insurance solutions.
- •Ashley's prior failure in insurance gave her authentic credibility with freelancers and deep understanding of their actual pain points, allowing her to position With Jack as a genuine solution rather than a speculative product.
- •By bootstrapping through her own freelance photography business instead of raising external capital, she maintained independence to build slowly without investor pressure and could validate the market with real skin in the game.
- •She correctly identified that insurance is a painkiller (essential risk mitigation) rather than a vitamin (nice-to-have), which meant her target customers had urgent motivation to adopt despite the friction of a regulated industry.
- •Her public transparency about both failures and competitive threats built trust with early adopters and differentiated her as a founder who prioritizes vision execution over defensive reactions.
- 1.Start by working in the industry or role you plan to serve—use your own business or job to experience the exact pain point you're solving and build credibility with potential customers.
- 2.Bootstrap the initial product using revenue from a parallel business (freelance work, consulting, etc.) so you can validate demand without investor timelines forcing premature scaling decisions.
- 3.Position your solution as solving an essential problem (painkiller) rather than a nice-to-have, and validate this positioning directly with early-adopter customers in your target segment before scaling.
- 4.Build in public about both your successes and failures, particularly how you handle competitive threats or setbacks, to attract customers who value transparent, principled founders over defensive messaging.
Similar Companies
247.ai
$25.0M/mo247.ai, founded by PV Cannon in 2000, is an AI-powered customer service automation platform serving over 150 enterprise customers with $300M+ in ARR. The company raised only $20M from Sequoia (2003) and bootstrap, achieving 10% net profit margins while maintaining a 12-month CAC payback period and 100% net revenue retention. Despite a security breach setback around 2018, 247.ai has recovered and recently achieved 20% new revenue booking growth in their best quarter.
iCIMS
$13.3M/moiCIMS is a bootstrapped SaaS provider founded in 1999 that dominates the talent acquisition software market as the #2 player, serving 3,500 enterprise customers with an average monthly spend of $4,000. The company exited 2017 with $160M ARR and is targeting 25%+ annual growth while maintaining profitability, recently acquiring Text Recruit to expand into candidate messaging and recruitment advertising.
Zoom
$12.0M/moZoom is a freemium SaaS video conferencing platform founded by Eric Yuan in July 2011 after he left Cisco to build a next-generation collaboration solution. The company has grown to 850,000+ paying customers across individual, SMB, and enterprise segments, generating over $12M in monthly recurring revenue with approximately 100% year-over-year growth. Rather than focusing on customer stickiness or aggressive growth targets, Zoom emphasizes customer happiness and organic word-of-mouth acquisition, which has proven highly effective in driving viral adoption.
Madwire
$10.0M/moMadwire is a comprehensive SaaS platform for small businesses (1-100 employees) that combines CRM, payments, invoicing, billing, e-commerce, and multi-channel marketing tools in a single platform. Founded in 2009, the company has grown to $120M ARR serving 20,000 customers with an average revenue per user of $500/month, while maintaining strong unit economics ($3,000-$4,000 CAC with 3-month payback) and recently turning profitable with a focus on reaching 15-20% EBITDA margins. The company is exploring an IPO within 12-18 months without having raised substantial capital beyond an initial $7.5M.
SwiftPage
$7.0M/moSwiftPage is a CRM and marketing automation platform founded in 2001 that targets small businesses. Under CEO John Oshel's leadership since 2012, the company scaled from 60,000 customers with $26.2M revenue in 2015 to 84,000 customers today with an estimated ARR of $36M+, maintaining 1.5% monthly logo churn and a 6-7 month payback period with a sub-$500 CAC.