Not My First Guess – Details, episodes & analysis

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 journey
• Insider tips on SEIS/EIS and equity investment
• Strategies for finding the right investors for your startup
• Lessons learned from co-founding and exiting successful tech start-ups
• How to think about valuing your early stage startup
• What Sam looks for as an angel and what really puts him off even a seemingly “great” deal

So, 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:

1. All about valuation:                                      https://www.foundercatalyst.com/blog/all-about-funding-round-valuation-2
2. Toxic Term sheets:                           https://www.foundercatalyst.com/blog/avoiding-toxic-term-sheets-everything-you-ever-wanted-to-ask-answered
3. Understanding how an angel thinks: https://www.foundercatalyst.com/blog/understanding-how-angel-investors-think-2
4. The end of an angel investment: https://www.foundercatalyst.com/blog/the-end-of-an-angel-investment-from-the-magic-to-tragic-2
5. Founder Catalyst:                                                 https://www.foundercatalyst.com/company
6. Sam’s LinkedIn:                                            https://www.linkedin.com/in/samsimpson1/?originalSubdomain=uk

🚀 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 path

Don't miss it! #Entrepreneurship #StartupLife #FounderStories #fintech #startups #innovation #podcast

Links:

• Coconut: https://www.getcoconut.com/

• Adam’s LinkedIn: https://www.linkedin.com/in/adamjgoodall/?originalSubdomain=uk

This episode we are joined by Nicola Ward, Co-Founder of CakeDrop. Having both worked in the City, Nicola and her sister Anna had a conversation about how awkward office birthdays can be. Often forgetting to buy a cake and having to resort to a cheap last minute one from the shop around the corner. They felt that something needed to be done to improve the employee experience in the office and uplevel celebrations at work. This gave way to the idea for CakeDrop. CakeDrop began by delivering artisan cakes to offices for employee birthdays, supported by an online calendar that allowed office managers and HR teams to pre-schedule key dates for the year ahead. 7 years on, and CakeDrop have worked with customers such as Disney, Meta, Netflix and LadBible.

In this episode we discuss:

• Evolving her business idea
• Running a business with a sibling
• How CakeDrop began and how they got to where they are now
• How they reacted to lockdown
• Building a team and finding the right people
• Learning the difference between how your gut is leading you and how your anxiety is leading you to make decisions
• Public speaking and founder confidence 
• The importance of momentum in fundraising
• Managing your potential investor base

Link to the Cake Drop website:

• https://cakedrop.london/

This episode we are joined by Felicity Halstead, founder of the company GoodWork. GoodWork is a not-for-profit that works with employers to create employment opportunities for young people from marginalised communities. Having had experience in youth programmes, as well as working with social mobility organisations and supporting entry-level recruitment in her job, Felicity saw first hand that a young person’s results on paper are not an accurate representation of how that person would apply themselves in the workplace. So often organisations would focus on past performance rather than potential. This led to the creation of GoodWork as Felicity hopes to breakdown systemic barriers to create more opportunities for young people.

In this episode, we discuss:

• Preconceptions around what talent looks like and how to identify potential
• Transitioning from only working in the public sector to the private sector
• The importance of finding your community
• Fundraising in the charity sector
• The community interest company (CIC) route
• Being a LinkedIn topvoice
• The impact of having an ADHD and Autism diagnosis

Link to the GoodWork website:

• https://www.goodwork.org.uk/

This episode, we are joined by Robert Hayward, founder of GoodFX, an international payments B Corp that turns currency conversion into social good, using the profits they make every time their customers trade FX, to support charities and create meaningful job opportunities for refugees. For anyone who doesn’t know, The foreign exchange market, commonly referred to as the Forex or FX, is the global marketplace for trading currencies. Having spent 10 years in the city working in banking, Rob had started to wonder how he could put his skills to use and make a difference in the world. After initially rejecting an opportunity to work in FX, he realised that there could be a way to use some of the money the industry was making in lockdown to make a difference. This birthed GoodFX.

In this episode we discuss:

• Rob’s journey into entrepreneurship and how he used his skills learned in the corporate world to get there
• The intoxicating nature of working with a “big fish” company
• Using a business model as a vehicle for social change
• Raising money as a B Corp, and the value of B Corp applications
• The importance of having self value as a fundraiser
• The necessity of bootstrapping when making an impact business

Link to the GoodFX website:

• https://www.goodfx.co.uk/

   This episode, we are joined by the founders of Future Kind Collective, Alicia Grimes and Natalie Pierce. Having initially met when Natalie interviewed Alicia for a job, the two found themselves working in the same company on strategy and service design projects focused on culture change. What started as a working relationship soon blossomed into a friendship and the two bonded on a shared feeling that something wasn't quite right about traditional culture consulting and that a change was needed. Alicia and Natalie thought that a more holistic approach was called for, with a focus on a genuine care for the people behind the business, prioritising people over profit, with as much focus on employees as customers. These ideas paved the way for the Future Kind Collective to be born, where a team was built that focuses on turning around the Culture of companies to create a better environment for all involved, or helping startups create great cultures from day 1!

In this episode we discuss:

• How Alicia and Natalie met and the birth of Future Kind Collective
• Imposter syndrome
• The definition of Culture
• How founders can use values to make decisions about what they do and don’t do
• The importance of saying no as founders

Link to the Future Kind Collective Website:

• https://www.thefuturekind.co/

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

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 2022

In this episode we discuss:

• Tim’s journey into entrepreneurship and the surprising difference between selling to bigger and smaller organisations
• Why and how to successfully exit a business that you founded
• Co-founder relationships
• Becoming an Angel Investor 
• The importance of focusing on a customer market rather than investor market
• How Hattie and Tim met and the development of IfWeRaise

Tim’s Businesses:

Deeson:

• https://www.deeson.co.uk/

OpenDialog.ai:

• https://opendialog.ai/

If We Raise:

• https://www.ifweraise.com/

In this episode we’re joined by Amardeep Parmar, Co-founder of The Bae HQ which is the number one community for British Asian Entrepreneurs; curator of the Tedx Chigwell programme, and host of the Entrepreneurs Handbook. 

As if that wasn't enough, having written and edited hundreds of Articles around the subject of entrepreneurship, Amar is also an Angel Investor.

Before lockdown, Amar was a technology consultant, having graduated with an economics degree. However, when covid hit, Amar decided to invest his time into more creative interests and began writing articles online. He became the second-fastest growing writer on medium.com, second to Barack Obama. This paved the way for a new career whereby he was able to become a fulltime creator in 2021.

In this episode we discuss:

• The pressures of being and calling yourself a “creator” in the entrepreneurial world
• The importance of making and putting out content in order to learn
• Treating people like people, not putting them on pedestals
• Social intelligence
• Lessons learned from podcasting
• Angel Investing and advice for first time raisers

Checkout more of Amar’s content:

The Bae HQ:

• https://www.thebaehq.com/

The Entrepreneurs Handbook

• https://open.spotify.com/show/5nceulxUsr8jrJ2TdSEVOK?si=14ab888833a4470f

Mentioned Resources

• https://seedlegals.com/
• https://hatchenterprise.org/
• https://www.antler.co/

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 new
• Mistakes you make when starting a new business
• The importance of deciding whether you want your business to be scaelable
• What VCs want
• The importance of finding the right co founder
• Prioritising your personal life whilst running a business
• And so much more

Check 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