New Adventures 2019 - Ashley Baxter Idea to Execution and Beyond

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It's a funny thing to be watching a talk and feel proud for spending money. Ashley Baxter is a brilliant person and she handles my business insurance through her company With Jack. Normally that would be something that would annoy me, spending money on insurance, but Ashley makes it all so easy from the on-boarding and throughout all communication. So to see her on stage was brilliant and it just shows how honest she is, in her talk Ashley explained all kinds of mistakes she had made and things she learned only through hindsight. It was fascinating and I have so much respect for her, running a business is hard for anyone but could you imagine trying to run an insurance business with no investment and expect to take on the massive corporations? Here are my notes of the talk.

  • 44% of freelancers will experience a client not paying on time
  • Ashley is a solo founder, with no co-founder
  • Self funded by money from work as a photographer
  • “Better to be a solo founder than have the wrong team/co-founder for the sake of it”
  • Only full time employee, works with freelancers
  • “Are you working on too many things?”
  • Made mistake of not putting side projects on back burner
  • Was just one of many projects
  • “Because we have the skill set to work on ideas, it means we all get pulled in lots of different directions”
  • “Building projects to 60%/70% complete before getting bored and move on” (Sounds like me!)
  • “The problem you’re solving can evolve over time”
  • “That’s okay, for things to change and emboldened over time”
  • Problems that With Jack set out to fix:
  • - insurers aren’t investing money into technology
  • - 2 out of 3 customers are unhappy with the customer journey
  • “Most insurers acknowledge that advance in technology is a problem but few are willing to do anything about it”
  • “Shopping for insurance sucks”
  • “We just cross our fingers and hope we never have to use it”
  • “Nobody cares”
  • All want better stuff but no one is searching for insurance based on what technology stack it uses
  • Not solving a real problem
  • Ashley asked her customers “Why did you sign up?”
  • Lots of really nice answers
  • "Made me feel really good”
  • “Commenting on onboarding”
  • “Simpler and easier to understand”
  • “None of that told me why people wanted to use it”
  • “Stopped asking that” because the answers were nice but not useful
  • So instead asked “What benefit have you received since signing up”
  • “Widely different answers”
  • “More confident in business”
  • All conversations led to realising the idea was a bad idea. It is not about making it easy to buy insurance. It is in business of keeping freelancers in business.
  • “This shift in the way I looked at this idea changed everything”
  • Focus now on being a confident freelancer
  • More verticals. Creating a platform about keeping freelancers in business opens up more avenues than insurance
  • Don’t be precious about your idea
  • Stop thinking as an industry expert, think as the customer
  • Ask the right questions
  • Problems not about insurance industry, the problem solving was about customers.
  • “Make sure you’re asking the right questions”
  • Slight tweak opened answers up for emotional responses
  • Otherwise just massage your ego because of answering wrong questions
  • Validation before writing too much code
  • Need to know if people actually want what you build
  • Previous project was best looking app on the market for the industry. Became confident cider so refactored app with zero users. Made £0 and time consuming
  • “The playbook of starting small and testing ideas quickly and cheaply doesn’t apply to everyone”
  • “I’m building something in a regulated industry”
  • “If you’re building something in healthcare, financial then it becomes impossible to test small ideas”
  • “£10k+ for approval to work in industry”
  • So signed up as an affiliate first, so not needing to be approved. Test the waters
  • Couldn’t solve issue of tech. Start page looked amazing but got pulled off to an external site leaving customers confused and meant didn’t know who customers were
  • Couldn’t have customer conversations which is “the lifeblood”
  • Able to bypass FCA authorisation by asking for email process before on-boarding. Didn’t feel completely comfortable but was the only way to figure out what kind of businesses use it. Could have been anyone.
  • Because businesses use custom domains, able to collect hundreds of websites to build for specific type of business... freelancers
  • That’s how validation worked. Landing page was deeply flawed and embarrassing but defined target audience
  • Even if not same barriers to entry but “let’s face it most of the low hanging fruit has been done. We don’t need another to do list”
  • NomadList started as a spreadsheet now doing £30k+ monthly revenue
  • Ghost started as a blog post, several hundred thousand views in first week before Kickstarter
  • Shipping anxiety
  • “You have created something but feel this apprehension of sharing it with the world”
  • Can hinder momentum
  • “If there is one thing I have learned it is momentum is everything”
  • “In an ideal word I would have shipped with a suite of products, a dashboard because every aspect should be digital, instant quotes and cover, customer journey would be very polished [...] still isn’t how it looks, reality is launched with one product, manual quotes” “processed a quote on top of a volcano in Spain”
  • Hadn’t even built key parts at launch. Sending to Typeform to complete purchase
  • “How could I have launched like this”
  • “Become advocates of resisting the urge to over engineer”
  • If you’re having conversations with your customers then you will learn lots about them. Automatic wouldn’t do that
  • Conversion was very high
  • A competitor was 20% vs 40% conversion
  • Common confusion and questions people have to create content or tools
  • Tool about vulnerability of business
  • Freelancers don’t know which insurance, coming with irrelevant products
  • “Desire to launch with pixel perfect”
  • “Get into habit of shipping things”
  • “Is there a way to do this manually?”
  • You will discover problems after you launch, that’s a good thing
  • Use pipe drive for following up with people
  • Iterate for collecting customer feedback
  • If somebody gets a quote but doesn’t buy then followed up with an email from real person
  • Two weeks later another email, to extract barriers
  • Response rate for open feedback is really low, more success with surveys
  • Personalising email as much as possible
  • Only 3 questions in survey, to know it only takes a minute or two
  • Mentioning being a small business shows not a big faceless corporation
  • 9% higher response rate than open ended feedback
  • “I discovered you all like the cheapest products
  • “I don’t want to be the cheapest I want to be the best”
  • Able to use survey to go to insurer to explain how many customers they are loosing
  • “There will always be a point where it is really hard and really not fun”
  • Book “The Mom Test will help you learn how to speak to your customers”

Feel free to read the rest of my notes from New Adventures.