Not My First Guess

Hattie Willis

Candid lessons from fellow founders, investors and innovation experts; to help you test, launch and scale your idea faster. read less
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From Pitch to Payday, The Hidden Costs of Fundraising: Featuring Sam Simpson
15-07-2024
From Pitch to Payday, The Hidden Costs of Fundraising: Featuring Sam Simpson
Have you ever found yourself drowning in fundraising legals and language? This is the interview you’ve been waiting for… In this episode, we're joined by the brilliant Sam Simpson, Co-founder of FounderCatalyst, who's on a mission to simplify and accelerate the early-stage investment legal journey. Sam's not just talking the talk; he's walked the walk, having co-founded and exited several tech start-ups, including the 17th fastest growing company in Europe in 2017. Oh, and did we mention he took that company from £0 to £27m in less than 4 years? But Sam's not just a founder; he's also an active angel investor with 32 investments under his belt in just 6 years. Plus, he's a sought-after board advisor. In other words, when it comes to navigating the minefield of fundraising and investment, Sam’s who you want to learn from.In this episode we discuss:Simplifying the early-stage investment legal journeyInsider tips on SEIS/EIS and equity investmentStrategies for finding the right investors for your startupLessons learned from co-founding and exiting successful tech start-upsHow to think about valuing your early stage startupWhat Sam looks for as an angel and what really puts him off even a seemingly “great” dealSo, whether you're a first-time founder trying to wrap your head around the legal jargon or a seasoned entrepreneur looking to optimise your fundraising game, this episode is packed with actionable advice and hard-won wisdom. Don't miss out on this incredible opportunity to learn from one of the people I trust most in this ecosystem!Links:All about valuation:                                      https://www.foundercatalyst.com/blog/all-about-funding-round-valuation-2Toxic Term sheets:                           https://www.foundercatalyst.com/blog/avoiding-toxic-term-sheets-everything-you-ever-wanted-to-ask-answeredUnderstanding how an angel thinks: https://www.foundercatalyst.com/blog/understanding-how-angel-investors-think-2The end of an angel investment: https://www.foundercatalyst.com/blog/the-end-of-an-angel-investment-from-the-magic-to-tragic-2Founder Catalyst:                                                 https://www.foundercatalyst.com/companySam’s LinkedIn:                                            https://www.linkedin.com/in/samsimpson1/?originalSubdomain=uk
From Entrepreneur to Employee: Lessons From Coconut Founder: Featuring Adam Goodall
01-07-2024
From Entrepreneur to Employee: Lessons From Coconut Founder: Featuring Adam Goodall
🚀 What’s it like to go Corporate Employee> Founder > Founder > Corporate Employee? At Not My First Guess we love a squiggly career path! 🏁That’s why we’re so excited to have serial founder, and once again corporate employee, Adam Goodall share his journey and lessons learned, from taking the first leap into full-time entrepreneurship, to deciding when to sell, to why he's enjoying being back in someone else's company. 🌐💡Adam is a serial founder with two startups under his belt - ProConfirm and Coconut. With a background in accounting at PwC, Adam has focused on innovating in spaces that may not seem “sexy” but have huge potential for growth. Adam first co-founded a startup with his room mate Samuel O'Connor (who he would also co-found Coconut with too), when their work at PwC led them to spot an opportunity to digitise the manual process of verifying client finances.They originally built ProConfirm as a side hustle while working corporate jobs but one of Adam’s biggest lessons was when to take the leap to full time. They soon gained traction, leading to acquisition interest from a major U.S. player.  Post-acquisition, Adam discovered his love for product management, setting him on the path to their next venture, Coconut, on a mission to simplify tax and accounting software for sole traders, landlords & their accountants. Since selling Coconut, Adam has now returned to employee life at Funding Circle and is brilliantly honest about what it was like to try to get a job as a serial founder (the hard and easy bits).🧠 Together we’ll explore:- How to find great ideas, when you are and aren’t looking for them- Adam’s hard won lessons on fundraising for Coconut, even as a second time founder with an exit under his belt- How to know when an acquisition offer is right for you- Advice on validating your idea before building the right product: what an MVP should and shouldn’t be- And how we build a robust identity as founders so we can fully embrace a squiggly career pathDon't miss it! #Entrepreneurship #StartupLife #FounderStories #fintech #startups #innovation #podcastLinks:Coconut: https://www.getcoconut.com/Adam’s LinkedIn: https://www.linkedin.com/in/adamjgoodall/?originalSubdomain=uk
How Every Founder Can Use AI: Featuring Cien Solon
17-06-2024
How Every Founder Can Use AI: Featuring Cien Solon
Are you worried you’re not using enough AI as a founder? I promise you’re not alone. In fact, after interviewing our incredible guest today, I went away and automated a LOAD of my own processes - sometimes you just need to understand the art of the possible!This episode is a GREAT start - we’re joined by AI advocate Cien Solon, who is on a mission to make “AI for All” with her latest startups Launch Lemonade and Scale that Thing! Cien is a Product-Led Growth expert, a start-up consultant and a constant builder. She is also a Techstars mentor and part of the Angel Investing School team.She has developed a portfolio of products from fintech, to AI tools to B2B SaaS and had a previous career in Marketing giving her an amazing view of the full journey.Today, with Launch Lemonade, she allows anyone to build AI chat bots to help with very specific tasks - from a sales chatbot to speak with customers, to creating marketing copy, writing reports, the possibilities are mostly bound by our own creativity; that’s why her consultancy startup Scale that thing helps  businesses build their AI and Product-led Growth strategies and implement them.So in this episode, as well as product building insights and advice  from an incredible expert, expect plenty of inspiration on how you can implement AI in your own business!Links:Cien’s Website:https://ciensolon.com/Launch Lemonade App:https://launchlemonade.app/Scale That Thing Website:https://www.scalethatthing.com/
Becoming Business Barbie and Making Accounting Accessible for Founders: Featuring Rachel Harris
04-06-2024
Becoming Business Barbie and Making Accounting Accessible for Founders: Featuring Rachel Harris
As well as being “Business Barbie” to her followers on instagram, Rachel Harris, is an award-winning content creator, author, speaker, business owner, and most importantly, an accountant extraordinaire. Named as one to watch on the 35 under 35 list and recently crowned as the First Intuition Apprenticeship Mentor of the Year for 2023, Rachel is a true breakout star in the accounting world.Rachel's passion for empowering accountants and small business owners shines through in her remarkable journey. From building the thriving Accountant She  community of over 25,000 people to becoming the youngest-ever director and trustee of AAT, Rachel has been a trailblazer at every step. She’s also making an impact, including with her innovative corporate bursary scheme, launched in January 2023, fully funds aspiring accountants in financial hardship, providing them with the mentoring and support they need to succeed.In this episode, we dive deep into Rachel's entrepreneurial journey and the invaluable lessons she's learned along the way. We'll explore:The power of community-building and creating the support system you wish you hadWhat founders do and don’t need to worry about when it comes to accountsThe most efficient way to pay yourself as a founderThe importance of setting an “internal charge out rate” to value your own time both in the company and out of itApproaches to valuing your company, and what Rachel looks for as an Angel Investor, and trains clients to prepare for in her mock “Dragons Den” investment readiness sessionsLinks:Rachel’s business StriveX:https://strivex.co.uk/Accountant_She Website:https://www.accountantshe.co.uk/Rachel’s Instagram:https://www.instagram.com/accountant_she/?hl=en
The Beauty of AI For Good: Featuring Simi Lindgren, Founder of Yuty
06-05-2024
The Beauty of AI For Good: Featuring Simi Lindgren, Founder of Yuty
This episode we are joined by Simi Lindgren Founder of Yuty. Some of you may recognise Simi from our special episode on fundraising as an underrepresented founder, where she was joined by two other incredible guests. But we wanted to take the time to dive deeper into Simi’s story and insights building an AI startup. Simi initially went to med school thinking that she would become a doctor. However, she soon realised that she wasn’t there for the right reasons. This led her to dropping out of her degree and getting an internship at a magazine working in beauty, and ultimately leading her to following her own passions. Simi then built up her experience in the beauty industry, working in marketing communications where she matched brands and PRs with media celebrities and influencers. Having progressed really well, in 2020 she decided that it was time to do something herself, which led to the launch of Yuty.Founded in 2020, Yuty is a venture capital backed technology company that uses AI to redefine hyper-personalisation, transforming the way brands can engage with their customers. The app provides data backed product recommendations delivered through a quiz, in order to help all customers, regardless of race, gender or ability, to find the product that is right for them. Having had personal experiences of not feeling seen or understood, and not being able to find the right products, Simi wanted to create something that was accessible for all, and after teaching herself to code, Yuty was formed.This episode we discuss:Choosing a path for the wrong reasons and going off the “beaten path” despite pressure internally and from the familyWhy she went down the VC route with YutyChoosing an Investor Partner and how to manage themThe importance of constantly asking questionsAssumptions and why being curious is the ultimate founder traitPlus much much more!Links:Yuty website: https://www.yuty.me/
Strands of Success: From Instagram Community to Industry Game Changer: Featuring Kate Berski
29-04-2024
Strands of Success: From Instagram Community to Industry Game Changer: Featuring Kate Berski
This episode we are joined by Kate Berski, Co-Founder of Curlsmith, a high performance, inclusive haircare brand which she started with her husband in 2018. It soon became one of the fastest growing textured hair brands and would go on to retail at Ulta Beauty, Target, Boots and many more. The idea for Curlsmith was formed out of a family struggle to find suitable haircare products for Kate’s nieces’ curly hair. Kate and her husband Michal soon realised that there was a gap in the market with lots of people unable to find appropriate products for their hair. Using her experience in advertising and brand consulting, combined with Michal’s experience working for some major beauty companies, they soon developed a community around an Instagram page that they launched, which shared advice, recipes and tips for people with curly hair, before they began the process of making their own product.In this episode, we discuss:The haircare industry and how Curlsmith was brought to lifeThe journey (and cost) of developing a productThe pros and cons of staying lean as long as possibleDigital vs retail channelsGoing down the VC route and how that helped grow the businessThe toll a startup has on your mental healthHaving a kid whilst running a business, and realising there’s more to life than workWhat it’s like to sell your company How entrepreneurship compares to becoming an authorAnd much much more…Links:Kate’s Instagram: https://www.instagram.com/kate.berski/Curlsmith website: https://uk.curlsmith.com/
Fertile Ground for Founders: Changing Lives and Welcoming New Ones: Featuring Tess Cosad
22-04-2024
Fertile Ground for Founders: Changing Lives and Welcoming New Ones: Featuring Tess Cosad
This episode, we are joined by Tess Cosad, the CEO and Co-Founder of Béa Fertility. As someone who takes much of her inspiration from injustice, Tess saw the pain and difficulties that many people were going through in their attempts to build a family, with access and affordability making the journey even more stressful and heartbreaking for many. In comes Béa Fertility, a company that provides clinical-grade fertility treatment that can be shipped straight to your door, and costs 1/20th of what IVF would.Tess has always been passionate about building businesses that make an impact. She was the first woman to lead a digital startup program to female entrepreneurs in Saudi Arabia in 2018, and is also a pioneer of the FemTech industry having gained experience working with Hers By Design, and Emberson Ventures, a B2B marketing agency.Despite often being one of the few women in male-dominated VC circles, Tess persists in her commitment to bring about positive change and support impactful solutions, by pushing evidence-based strategies and supporting founders who adopt similar change driven principles.This episode, we discuss:Mistakes and lessons learnt from Tess’s previous start-up venturesThe importance of speaking to your users/customersThe importance of storytelling and how this became Tess’s skillsetWhy being the keeper of the context is your most important role as CEO of a startupThe process of finding mentorsThe struggles of finding investors and raising funds, and the importance of keeping your passion throughout the processAnd much more including hilarious stories that had our editor chuckling almost the whole way through the edit!Let us know what you think!Links: Bea Fertility website Brad Feld’s book Venture DealsFounders Pocket Guide to term sheets
Rethinking Start-up Funding for more Equitable Entrepreneurship: Featuring Andy Ayim MBE
15-04-2024
Rethinking Start-up Funding for more Equitable Entrepreneurship: Featuring Andy Ayim MBE
This episode, we are joined by Andy Ayim MBE, a serial founder and Angel Investor who is known for his human centered approach to business. Over a decade ago, Andy cofounded Mixtape Madness, a proudly bootstrapped 7 figure business. When he left day to day operations there, he dove into Product Management with high growth startups such as WorldFirst, acquired for $700m by Ant Financial; and Series C startup Zilch where he was Head of Product Management. In 2018 he took his next leap, to become Managing Director at US based VC firm, Backstage Capital where he raised over $2.5M to deploy into underrepresented founders.As you’ll hear, improving equity in the startup ecosystem has been a huge driver for Andy, and led to his next startup, The Angel Investing School, a company on a mission to train the next generation of angel investors, including those who feel excluded by the current system, or haven’t seen typically  themselves represented among angels. Additionally, Andy supports startups, scaleups and corporates as an advisor; this is someone who knows what it takes to grow a company. Andy’s impact has seen him get voted as one on the top 10 BAME Leaders in Tech in the FT, as well as being awarded an MBE for his services to diversity in tech.Andy has also been one of our biggest supporters at IfWeRaise from the very early days, in fact even before I met my co-founder, and is now one of our Board Advisers, so it was extra special having him on the show.In this episode, we discuss:Andy’s personal user guide as his intro into the world of entrepreneurship (and why we probably all need one)Why Andy created Angel Investing School and how it’s evolvingThe importance of building social capital and a personal brand as a founderWhy fundraising isn’t always the best optionWhat Andy looks for in founders from an Angel's perspectiveThe importance of storytelling and how to nail itThe backwards relationship we have with failure in the UKLinks:Angel Investing School:https://angelinvestingschool.com/Andy’s Personal User Guide:https://andyayim.com/my-personal-user-guide/Mixtape Madness:https://www.mixtapemadness.com/
Business and bipolar: changing the future of mental health support, with James Roycroft-Davis, Co-Founder of Baseline
16-01-2024
Business and bipolar: changing the future of mental health support, with James Roycroft-Davis, Co-Founder of Baseline
In this episode we’re joined by James Roycroft-Davis. James is a Serial Founder, Angel Investor and Host of the UK’s #1 Founder and Investor Mental Health Podcast - Vulnerable.He’s previously started businesses around weightless and dog training, but hadn’t yet found his purpose and the business he wanted to build for the next 10 years, until in March 2023 he was diagnosed with Type 2 Bipolar Affective Disorder. When he started sharing about his diagnosis on his social media he was flooded with messages saying “there’s no support for me or my support networks”.It’s what led him to co-found Baseline, as he puts it:The first company building technology, content, and community in the Bipolar space, to help people on the bipolar spectrum and their support networks to live better. In this episode we dive into: - Why first time founders need to stop giving investors god like status- The shocking correlation between founders and the Bipolar spectrum- How getting his diagnosis led to Baseline- Building your first product on a shoestring with AI- The importance of building for mental health sustainability as a founder- The need for founders to nail content creation and personal branding- And much more!James’ Business Baseline:https://www.joinbaseline.co/James’ Podcast, Vulnerable:https://open.spotify.com/show/1K0x3TuxwlV8lhRhMJzcSD?si=3b8cb3208ce34ca2
How to successfully exit your own company, with Tim Deeson
09-01-2024
How to successfully exit your own company, with Tim Deeson
This episode, we're joined by Tim Deeson, serial founder and angel investor with over 20 years of experience building companies. He started his first company Deeson, which grew to be a multi-million pound digital agency, at age just 20. Tim successfully exited Deeson to co-found GreenShoot Labs, an innovative conversational AI consulting and product development studio. After exiting that, Tim became an Angel Investor and took up a role at LSE as an entrepreneur in residence, giving advice to students, alumni and staff on their start up ideas and business. Alongside all this work, Tim started to feel the founder itch again, and so it was really lucky that when we met he ignored Hattie's initial attempts to tell him he could not be her co founder, because they were increasingly sharing the same mission of how to make access to the startup ecosystem fairer. Ultimately this led to the beginning of IfWeRaise, a company that Tim and Hattie co-founded in 2022In this episode we discuss:Tim’s journey into entrepreneurship and the surprising difference between selling to bigger and smaller organisationsWhy and how to successfully exit a business that you foundedCo-founder relationshipsBecoming an Angel Investor The importance of focusing on a customer market rather than investor marketHow Hattie and Tim met and the development of IfWeRaiseTim’s Businesses:Deeson:https://www.deeson.co.uk/OpenDialog.ai:https://opendialog.ai/If We Raise:https://www.ifweraise.com/
Banker to changemaker: empowering SMES in emerging markets featuring Alberta Asafo-Asamoah, Co-founder of Liquify
14-12-2023
Banker to changemaker: empowering SMES in emerging markets featuring Alberta Asafo-Asamoah, Co-founder of Liquify
Today I’m joined by Alberta Asafo-Asamoah, a social entrepreneur and educationalist, and co-founder of Liquify, an invoice marketplace that enables SMEs in emerging markets to get quick access to affordable cash.Having started her career building deep expertise in the financial world, Alberta left banking in 2018 to pursue a career in impact investing because she wanted to combine her knowledge and experience in financing, with her passion for social issues and social change. This led Alberta to founding Algebra In The City (AITC), an educational tuition and consultancy business. Having spent some time as a tutor, Alberta had seen a disparity between students that went to private schools and students who went to state schools, including differences in the way students had been taught to process information and problem solve. This led Alberta to wanting to make education more equitable for young people by making tuition much cheaper in order to increase accessibility.However, one of the things we dive into in this episode is Alberta’s desire to build something at scale- and once she realised this wasn’t the business she wanted to be building for the next 10 years, it was time for a pivot to build something more VC backable… one that ultimately led her to liquify.In this episode we talk about:Internships and the importance of taking a step back when you’re starting something newMistakes you make when starting a new businessThe importance of deciding whether you want your business to be scaelableWhat VCs wantThe importance of finding the right co founderPrioritising your personal life whilst running a businessAnd so much moreCheck out Alberta’s company Liquify:https://liquify.digital/Check out Algebra in the City:https://www.algebrainthecity.com/about-us/WMassive thank you to this episode’s sponsor ShipShape. If you want to tailor your search for VCs, check them out at www.shipshape.vc
Fundraising Special Part 2 (Back By Popular Demand)
28-11-2023
Fundraising Special Part 2 (Back By Popular Demand)
This episode is a little bit special. We're doing our second fundraising compilation, taking different tips and hard won lessons from our founders we've interviewed before. In this episode, we're going to focus on five founders:1. Jay Richards: At the time of interview, Jay's company Imagen had 25, 000 community  members across 111 countries, having raised just 400k. Incredible growth. Here Jay talks about how some founders have a grit that means they can just go further with less. Curious about Imagen? Learn more here: https://imageninsights.com/2. Valentina Milanova: Valentina has raised several rounds of funding for her femtech company Daye, including a 10 million series A. In this episode she talks about her experiences fundraising as a female founder as well as some of the things she did but maybe wouldn't do again. Checkout Daye’s website:  https://www.yourdaye.com/3. Lottie Unwin: Lottie is a proud bootstrapper who grew her business to over a million in revenue without fundraising. In this episode she shares her perspective and why she chose a different path. Since recording Lottie’s company have rebranded from CopyClub to Upworld. See more of what they’re up to at https://up-world.co/ 4. Joyeeta Daas: Joyeeta is a serial founder who created five startups and successfully exited three. Since the episode aired, she's fundraised again for her most recent venture, Samudra Oceans: https://www.samudraoceans.com/5. Eliot Brooks: Eliot grew health tech startup Thriva to over 100,000 customers and more than 130 staff before he decided it was time for his next startup adventure. Before he left, Thriva had raised 11 million pounds in funding based on 100 percent year on year growth rates: Thriva | Home Blood Testing & Health ChecksTogether they cover a huge range of business models and industries. From B2B SaaS to HealthTech and FemTech, Community plays, DeepTech and ClimateTech.Want to dive in deeper- checkout each of the guests’ full episodes:Jay Richards: https://open.spotify.com/episode/4o0lQfU69vC8HEYzdfs4wb?si=de2a9f708a864d2bValentina Milanova: https://open.spotify.com/episode/4jfFTiaD2hRyiuCHUaproV?si=2c4584b088ce47d3Lottie Unwin: https://open.spotify.com/episode/2iRxjMLNUXviNhpVPJXmiE?si=293d0b1e872140b4Joyeeta Daas: https://open.spotify.com/episode/2NV8fCzOUKaGSU0xeUQwMJ?si=8d3a33cf63334748Eliot Brooks: https://open.spotify.com/episode/3bfYSOaUSL9Fxf9xP6IxIZ?si=2df55b95df004a1eFinally, a massive thank you to this episode’s sponsor ShipShape. If you want to tailor your search for VCs, check them out at www.shipshape.vc
What VCs don't tell you when you're raising with Jasmin Thomas, serial Founder & Angel Investor
18-09-2023
What VCs don't tell you when you're raising with Jasmin Thomas, serial Founder & Angel Investor
Today I’m joined by Jasmin Thomas, Serial Founder & Angel Investor.After a successful career building the first teams of unicorns like Deliveroo, Algemy, Improbable and Dark Trace, Jasmin turned her hand to her own business.Having been diagnosed with MS, Jasmin had experienced the benefits of CBD oil first hand, from relieving period cramps to flare ups she was having.From this, she was inspired to start her own efficacious skincare company, Ohana Health. However, as she soon found out, having a CBD based product brings even more challenges than your regular startup. And once she realised it wasn't a VC backable business, she made an even bolder move to shut the company down.Now, she uses the valuable insights she gained through that experience, along with a deep passion for supporting women in various capacities, particularly early stage founders and those in the tech industry, to fuel this next phase of her career.Her dedication is channeled through her work with angel community Alexandria Angels, where she focuses on investing in exceptional deal flow at the early stages, aiming to diversify cap tables, as well as acting as a venture partner and scout for VCs and as a consultant, collaborating with pre Series A startups.She's also committed to supporting the development of gender diverse tech teams, bridging the gap for women in tech and STEM fields with tech recruitment agency Xena.In case you couldn't already tell, she's a rather remarkable leader in the community and has even been highlighted by Richard Branson as an entrepreneur to watch for her exceptional drive and vision.In this episode we discuss:Thinking out of the box as a core founder skillAsking VCs the right questions while you raiseThe secret value recruiters bring to the tableHow intention and self-awareness lead to successUnearthing hidden hurdles in your industry, earlyAnd so much more!Links:Check out Alexandria Angels - https://alexandriaangels.persona.co/Learn about Angel Investing from Andy Ayim - https://andyayim.comCheck out We Are Xena - https://wearexena.comListen to our episode with Alexia Baron - spoti.fi/3EhjhXhListen to our episode with Jacqui -Check out our new sponsor shipshape.vc - https://bit.ly/43Kq99N