Continuing the Series 2 strong start, we dive into an exhilarating conversation with Jamie Haymer, the entrepreneur who transitioned from a thriving media subscription venture, into the intricate world of insurance and risk management.

Jamie's trajectory is impressive, from his foundational days of selling educational books door-to-door before spending time with Proctor & Gamble and Gartner, to his rapid success with React News, which exited within its first two years, to his latest endeavour, Bolt Warranty.

This episode is a goldmine for startup founders, offering deep insights into Product-Market Fit, growth indicators, early-stage funding nuances, and the unmatched value of referral hiring and data-driven strategies.

Whether you're deep into your startup journey or just starting out, this episode promises invaluable takeaways. Here are the highlights.

(01:50) - Jamie's background and early entrepreneurial days.

(06:50) - The boredom cliff: Transitioning from a secure corporate job to a startup life.

(11:49) - The importance of a good pitch deck early on.

(13:28) - Finding early backers' initial funding and giving away more than you need to.

(17:01) - Understanding the tax breaks for UK startups and SEIS.

(19:04) - The early days and the value of working with consultants.

(21:12) - Knowing when you've got Product-Market Fit (PMF).

(26:27) - The threat of competitors and keeping a close on how they reacted once we launched.

(28:23) - Being acquired within 20 months of launch and the importance of a good product lead and monitoring usage data.

(33:15) - The idea of Feature-Market Fit and building products the market doesn't use.

(36:45) - Being approached and acquired within 6 months of initial contact and the mixed emotions of exiting.

(40:37) - Moving from one success to starting his second business, Bolt Warrantly, operating within the Insure-Tech sector.

(42:55) - What Jamie is doing differently this time around and the importance of user research.

(44:22) - Advice to founders just starting out and not going alone, including where to find those first early hires for your business.

(46:12) - Working with technical agencies to build your early product and how to go about choosing the right partner.

(48:52) - Behind Startup Lines question: best strategic manoeuvre.

(51:55) - The help Jamie is looking for and how to get in touch.

For more information:

LinkedIn: https://www.linkedin.com/in/philipguest/

Website: https://www.revcelerate.com/

Twitter:  https://twitter.com/PhilGuesty

Dive back into the tenacious world of startups with a fresh episode of Behind Startup Lines. This episode kicks off our exciting second series, broadening the spectrum of innovative startup narratives.

Join us as we explore Dr. Jessica Pely’s transition from a scholar in finance and behavioural economics to becoming the CEO and co-founder of Loyee, a platform transforming the sales lead qualification process.

Jessica shares the essence of understanding your customer’s customer, honing focus, and strategies for clinching those initial crucial sales.

Plus, stay tuned till the end for insights on a new Go-to-Market (GTM) assessment tool that could be a game-changer for startup founders grappling with market entry strategies.

A conversation rich in experience and insights, this is a ride worth buckling up for!

(02:59) Introduction to Jessica’s background and her company Loyee.

(06:30) Lessons from her first two startups applied to building the current business.

(09:40) How having a background in computer engineering helped and the value of working with a deviated technical lead.

(14:08) Moving the business from Germany to the United States and winning the right customers in a new market.

(17:40) The value of recruiting design partners as a way to build traction and win early customers.

(19:45) The importance of having clearly defined personas and the level of detail in determining them.

(21:28) The importance of understanding your customer's customer.

(25:00) Sales, from a Numbers game to a Fit game, and the importance of focus and trade-offs.

(31:18) Key lessons in scaling a business during a tumultuous year.

(34:48) How the buyer cohort has shifted and the challenges of aligning a larger buyer cohort to secure a sale.

(40:40) Working within a stage-appropriate sales framework that can adapt.

(45:00) My advice on how to align customer stakeholders.

(49:54) The current investor environment and raising through Safe Notes.

(56:08) How to get in touch with Jessica and Loyee and final advice for founders who are building their business and the need to follow your instincts.

Lastly, details about my new GTM assessment that can be accessed at https://www.gtm.revcelerate.com. Take this short quiz to benchmark your current GT< strategy and advice on what you can do to take it to the next level.

For more information:

LinkedIn: https://www.linkedin.com/in/philipguest/

Website: https://www.revcelerate.com/

Twitter:  https://twitter.com/PhilGuesty

Welcome back. In today's episode, we have a special guest, Kaisa Kromhof, the founder of Ment, a revolutionary no-code document automation technology.

Join us as we delve into Kaisa's journey, from her background as a corporate lawyer to her realisation that there must be a smarter way to work.

We'll explore how she turned her vision into a reality by creating her own document automation software and eventually selling her company to Mfiles. Kaisa shares valuable insights on building traction, securing funding, and navigating the challenges of entrepreneurship.

Stay tuned and be inspired by Kaisa's incredible journey from legal woes to no-code wins. Let's dive in!

(03:11) Origin story and the problem Ment sought to solve for legal teams

(08:16) Dealing with the challenge that your product already exists

(14:14) Timing and connecting the dots for the problem you want to solve and building your MVP.

(18:40) Discovering the missing ingredient that customers value most.

(23:10) Winning those first customers and strategies to consider to build credibility in your customers' minds.

(27:56) Customer tolerance towards the MVP and how to ensure they stay the course with you.

(32:50) Transitioning from founder-led sales to building your sales team while working with advisors.

(37:36) The importance of documenting the sales process early on with practical examples and the biggest learning about sales.

(45:10) How sales change when you have the backing of an established business. What is the same, and what is better.

(47:20) Knowing when you have Product Market Fit (PMF)

(50:50) Closing a funding round in two weeks when you hit PMF.

(54:10) How the acquisition came about through collaboration even though Kaisa was not contemplating a sale.

(57:50) Key lessons and the mindset for building the next business.

(1:01:32) Behind Startups Lines quick fire question - how to bounce back from a setback.

(1:03:11) How to get in touch with Kaisa.

For more information:

LinkedIn: https://www.linkedin.com/in/philipguest/

Website: https://www.revcelerate.com/

Twitter:  https://twitter.com/PhilGuesty

In this episode, Guillaume Descottes, the founder of Vialma, a groundbreaking platform at the intersection of technology and music, shares his remarkable journey, starting from a career in Private Equity to the formation of Vialma.

Guillaume dives into the highs and lows of entrepreneurship, reflecting on the importance of ego and the impact of hiring talented interns on his business early on. With a passion for the arts and a desire to make a positive impact, Guillaume sheds light on Vialma's work in the digital music space.

He also delves into the transformative power of AI in the industry and the need for Europe to carve its own path to avoid being overshadowed by dominant American players.

Join us as we unravel Guillaume's intriguing insights into the music industry, entrepreneurship, and the intersection of innovation and impact.

Get ready to be inspired and informed in this captivating episode of Behind Startup Lines!

Highlights:

(04:59) Protect the value you are delivering to your customers  

(11:11) The importance of partnerships and how to make them work

(13:22) The impact of AI on the music industry

(18:20) Taking the leap from PE investor to start-up entrepreneur

(23:09) Your ego is probably your best friend and your worst friend 

(25:15) Being comfortable about being uncomfortable

(32:23) Remote working and finding the sense of purpose of working together 

(34:34) Not every customer has explicit pain points!

(35:32) The differences between doing business and innovation in Europe vs the USA

(38:36) The current state of startup funding in Europe

(43:33) Decrease the churn and increase brand engagement by linking customer KPIs

(45:01) Building trust and long-term relationships for the future

(51:03) Understand who influences the decision to buy your product

(52:50) Advice to founders about making the leap to starting a business

(56:57) The importance of having your product team talk to customers

(59:23) Quickfire Behind Startup Lines question: Marching to the sound of the drums

For more information:

LinkedIn: https://www.linkedin.com/in/philipguest/

Website: https://www.revcelerate.com/

Twitter:  https://twitter.com/PhilGuesty

In this episode, CEO and co-founder Tom Lavery shares his story of building Jiminny, a conversational intelligence platform designed to help salespeople be more effective.

Tom's story is interesting on many levels, not least that as a successful sales leader himself, he then turned to being a successful tech entrepreneur. While you might think that with his background in sales, Tom had an unfair advantage in winning customers. But as you're about to find out, that wasn't quite the case.

From Jiminny's origin story and the importance of researching your market, this episode covers the ups and downs of building a successful business. Tom shares insights such as strategies for winning first customers, differentiating the product, and the importance of mission and values in creating a strong company culture. Tom also shares his wisdom on investment strategies that worked for Jiminny and what to look for when you're making important sales hires.

Today, Jiminny has gone on to establish itself as a leader in the conversation intelligence sector, attracting hundreds of clients and significant funding to help the team build on their success. This is a truly compelling listen for anyone interested in becoming an entrepreneur and building a successful business.

Join me as Tom tells us how he did it.

Here are the highlights:

(02:14) Jiminny's origin story

(04:15) The importance of market research

(06:49) Getting started and forming the co-founder team

(08:20) Learning a new skill to build the product

(09:18) Winning Jiminny's first customers and charging from day one

(12:45) How to convince customers to buy into your unknown, unproven product

(15:44) Differentiating your product and establishing an unfair advantage

(17:52) Mission and Values as essential elements to hiring and building a healthy culture

(21:28) How to asses if a sales hire is really capable and a good fit

(24:28) What Tom would do differently when launching his next business

(25:24) How working with advisors can help an entrepreneur focus on what matters most

(26:55) Investment and the value of debt vs equity in the early days to grow

(29:04) Behind Startup Lines founder quick-fire question

(30:54) How to get in touch with Tom

For more information:

LinkedIn: https://www.linkedin.com/in/philipguest/

Website: https://www.revcelerate.com/

Twitter:  https://twitter.com/PhilGuesty

James offers us a fantastic insight to the investor sentiment and how weather the current storm. As an operator himself turned VC he has a unique view of what it takes to build a successful business, sharing practical strategies and tactics that he’s seen work for many of the startups he supports. 

Some of the key takeaways I picked up on are how to make the most of hiring an advisor, the importance of documenting the founder led sales process early on and how businesses should be incorporating AI into existing products. Full conversation notes below. 

I think you’re going to enjoy this conversation and if you do, please give it a ⭐️⭐️⭐️⭐️⭐️rating, thanks.

Phil

Here are your conversation highlights:

(01:43) The Good and Bad early stage business sales and GTM

(04:08) Becoming a VC after experiencing the hard knocks as a start-up operator himself 

(11:05) Integrating AI into existing products vs building an investable new AI product

(13:20) Surviving the current investment drought 

(16:32) Advice to founders who find selling uncomfortable or even distasteful 

(18:44) Building your first sales team 

(22:01) Making use of advisors and the importance of using retainers with context 

(26:37) The value of using a good sales structure like MEDDICC

(28:43) Driving awareness and lead generation strategies that actually work in the early days of building a new business 

(33:38) Quick fire questions – Playing the long game and markers of success, decision making to  maintain momentum, the types of business Portfolio Ventures invest in and how to get in touch. 

For more information:

LinkedIn: https://www.linkedin.com/in/philipguest/

Website: https://www.revcelerate.com/

Twitter:  https://twitter.com/PhilGuesty

In this episode, we welcome entrepreneur and angel investor, Rachel Belle, to share her wealth of knowledge and experience in areas including PR for startups, leadership, and angel investing. Rachel is candid about the challenges and triumphs of establishing and growing businesses, highlighting the essentiality of delegating tasks to make the biggest impact.

She offers insights into managing complex personalities in a team, emphasising the need for understanding and effective incentivisation. A renowned entrepreneur in residence at the London Business School, Rachel gives us a glimpse into her work there. In a revealing discussion about Enterprise 100, a private angel investment network, she explores how this platform is revolutionising funding support for early-stage businesses.

Rachel's own stories and reflections pepper the conversation, providing not only educational takeaways but also inspiring listeners with her entrepreneurial journey. Whether you're a seasoned business owner, an aspiring entrepreneur, or an interested observer, this episode with Rachel Belle promises to deliver meaningful lessons and motivating insights.

Highlights: 

(01:35) PR background, started successful businesses, now helps entrepreneurs.

(06:24) The catalyst for starting my first business - Late twenties, pitching success, Father's death lit a fire under me. Founded Shine Communications, designed to empower others.

(14:38) Early success, outsourcing, and learning from others.

(19:38) Dyslexia, education and expectations of me as a woman and how being competitive and overcoming fear of failure can be a driver.

(28:27) Being your authentic self and developing a buyer mindset to stand in your customer's shoes.

(32:17) Managing scale in your business by building a business unit model and managing your hardest-to-manage people by encouraging them to ask-me-anything.

(40:03) How effective is PR for early-stage businesses? The initial focus and the importance of trade press, events, and awards. Be aware there's no such thing as off-the-record.

(47:51) The value of relevant content to showcase your expertise and drive SEO. The importance of standing out by having an opinion and doing something different.

(55:14) Working as an Entrepreneur in Residence at London Business School. The importance of plans that you actually follow with a clear set of tactics.

(1:01:42) Why startups fail when you don't keep it simple, understand the basics.

(1:03:14) About the private angel investment network Enterprise 100 (E100) and how to get involved.

(1:08:34) Quick fire question: Guerrilla marketing - does it work, and how to go about it.

(1:12:25) Final words on the opportunity for all - be brave and ask for advice.

For more information:

LinkedIn: https://www.linkedin.com/in/philipguest/

Website: https://www.revcelerate.com/

Twitter:  https://twitter.com/PhilGuesty

Joe Mathewson is a founding partner and co-CEO of Firefly. A school management information system that he built with his co-founder Simon while they were still at school taking their GCSE exams.

After school, he joined UBS as a trader before going all in on Firefly to pioneer these school systems that, today, are very common. Back when he started, SaaS wasn't the dominant business model it is today, and Joe shares he hard learnt lessons on pricing and GTM.

Joe's story is fascinating, not least that his story is one from idea origination through fundraising to a successful exit when Veracross acquired Firefly. There is a lot to learn from this successful entrepreneur that I am sure you'll find interesting.

I hope you enjoy the show.

Phil

Here are some of the show highlights:

(2:24) Where it began

(6:34) Good products don't sell themselves

(10:11) Working with an external supplier for early lead generation

(13:34) First-hire failures

(17:04) Controlling the sales process

(18:41) Incentivising the team

(20:54) Sales team structuring

(23:38) Building the customer success function

(25:27) Introducing a Chief Revenue Officer to manage managers

(27:26) Navigating a successful exit

(33:38) What would you do differently next time - the value of advisors

(35:17) Making tough decisions

(37:48) Ensuring the team stay focused

(42:00) Where to learn more about Firefly and Veracross

Joe can be reached via his Linked~In profile

https://www.linkedin.com/in/joe-mathewson-2867162/

For more information:

LinkedIn: https://www.linkedin.com/in/philipguest/

Website: https://www.revcelerate.com/

Twitter:  https://twitter.com/PhilGuesty

Welcome to another exciting episode of "Behind Startup Lines", where we delve into the inspiring journey of Johann Malawala. As a former obstetrics and gynaecology clinician, Johann has expertly navigated the path from delivering babies to simultaneously delivering twin businesses – a unique blend of a not-for-profit and a commercial venture.

In this episode, Johann candidly shares invaluable insights gleaned from his unique career transition, offering a fresh perspective for those working in or selling into the healthcare or public sector. With a foot in both worlds – as a practitioner and an entrepreneur – he effortlessly bridges the gap between in-depth sector knowledge and business acumen.

Join us as we explore how to navigate complex sectors and balance commercial and philanthropic endeavours. This episode is a treasure trove of inspiration and practical advice for entrepreneurs, healthcare professionals, and anyone interested in making a meaningful impact in their industry.

Don't miss out on this compelling narrative of transformation, innovation, and entrepreneurial spirit on "Behind Startup Lines" - where we bring you real-life stories from the frontlines of entrepreneurship.

Highlights:

(13:25) Johann's entrepreneurial journey

(16:50) Simultaneously building a not-for-profit and commercial business

(19:40) Winning your first customer

(28:00) Complexities of mapping healthcare buyer cohorts

(33:55) How to work with the NHS health service

(38:00) Establishing your credentials and selling to the NHS

(58:00) Advice Johann would give his past self

(1:00:00) Behind Startup Lines quick-fire questions

(1:07:00) How to truly connect with people on LinkedIn

For more information:

LinkedIn: https://www.linkedin.com/in/philipguest/

Website: https://www.revcelerate.com/

Twitter:  https://twitter.com/PhilGuesty

Today’s guest is not our usual tech founder discussing software products. 

I’m talking to David Strang. 

David built a successful business in the toy and outdoor sports equipment field. 

However, in this episode, David tells us how it wasn’t all plain sailing. 

His stories will ring true for many of us as we build our businesses. 

So, join us today to hear some honest truths about making mistakes and gaining success. 

Here are the highlights:

(1:49) Best in the market

(4:27) Adapting products

(9:53) Starting over

(19:54) Recycling knowledge

(25:51) Winning 

For more information:

LinkedIn: https://www.linkedin.com/in/philipguest/

Website: https://www.revcelerate.com/

Twitter:  https://twitter.com/PhilGuesty