The Art of Exiting: Lessons from a Serial Entrepreneur

Huge thanks to Deel for sponsoring this episode. Learn how their people management software can streamline your global organisation here: https://bit.ly/4eZeJ88 ----------------------------------------- Check out Part One of this conversation here: https://youtu.be/bEY7wJT1qBc Welcome to Part Two of our conversation with David Graham. In this conversation, David Graham shares his career journey from exiting his first business to exploring new ventures, including consulting and building an EdTech company. He discusses the challenges of the EdTech landscape, the importance of market fit, and the realities of fundraising. David emphasizes the need for a strong value proposition and understanding investor expectations, while also reflecting on the balance between growth and maintaining control over one's business. In this conversation, David Graham and Greg McCallum discuss the intricacies of startup funding, focusing on the importance of understanding customer lifetime value (LTV), the stages of startup development, and the various forms of traction that can be demonstrated beyond just revenue. They emphasize the need for founders to build solid foundations and operational processes before seeking significant investment. Additionally, they introduce Directive, a service aimed at helping founders streamline their fundraising efforts, and discuss future plans for thematic accelerators to support startups in specific sectors. Chapters 00:00 David Graham's Career Journey: From Exit to New Ventures 02:59 Consulting and Business Turnarounds: Lessons Learned 05:53 The EdTech Experience: Building and Selling a Comms App 09:00 Navigating the EdTech Landscape: Challenges and Insights 12:06 Evaluating Business Ideas: The Importance of Market Fit 14:58 Investment Decisions: The Balance Between Growth and Control 18:09 Understanding Investor Expectations: The Use of Funds 21:05 The Reality of Fundraising: Time and Focus 24:02 Final Thoughts on Business Strategy and Investor Relations 35:39 Understanding LTV and Customer Acquisition Costs 39:55 Stages of Startup Development: From Pre-seed to Series B 47:10 Defining Traction: Beyond Revenue 51:30 The Role of Data in Fundraising 54:36 Introducing Directive: A New Approach to Fundraising 01:00:07 Future Plans: Thematic Accelerators and Support for Founders Follow David on LinkedIn here: https://www.linkedin.com/in/dguk/ Checkout Dyrectli Capital here: https://www.dyrectli.com/ Want a 1-hour free advisory session with me, Greg McCallum? 👇👇👇👇👇👇👇 https://meetings-eu1.hubspot.com/meetings/gmccallum?uuid=c7ed45d8-c8fe-4b6a-9eda-d062fd02c9ad

Huge thanks to Deel for sponsoring this episode. Learn how their people management software can streamline your global organisation here: https://bit.ly/4eZeJ88 ----------------------------------------- In Part One of this conversation, David Graham shares his journey as a four-time executive founder, discussing his early ventures in e-commerce and hospitality. He reflects on the challenges faced in the restaurant industry, the importance of creating a strong company culture, and the need for effective training in business. David emphasizes the lessons learned from his experiences and the evolving landscape of the hospitality sector. David Graham and Greg McCallum discuss the intricacies of team building, growth, and the challenges of remote work. They emphasize the importance of authenticity in team dynamics, the natural flow of growth in businesses, and the risks associated with scaling. The dialogue also highlights the significance of creating a culture of innovation, the role of informal interactions, and the necessity of mentorship for founders navigating their journeys. Chapters 00:00 Introduction to David Graham 01:58 David's Early Ventures and E-commerce Success 12:04 Transitioning to Hospitality and Catering 20:01 Challenges in the Restaurant Industry 25:10 The Importance of Culture and Training in Business 28:35 Authenticity in Team Building 29:32 The Natural Flow of Growth 30:31 Challenges of Remote Work 32:12 Momentum and Scaling Risks 33:34 Creating a Culture of Innovation 34:57 The Importance of Play in Work 36:45 Navigating Collaboration in Remote Settings 38:35 The Value of Informal Interactions 40:31 Maintaining Connection as Companies Grow 42:22 The Journey from Ideation to Series A 44:47 Hiring Strategies for Early-Stage Startups 46:39 The Role of Mentorship in Founding Success Follow David on LinkedIn here: https://www.linkedin.com/in/dguk/ Checkout Dyrectli Capital here: https://www.dyrectli.com/ Want a 1-hour free advisory session with me, Greg McCallum? 👇👇👇👇👇👇👇 https://meetings-eu1.hubspot.com/meetings/gmccallum?uuid=c7ed45d8-c8fe-4b6a-9eda-d062fd02c9ad

Welcome to Part Two of our conversation with Mark Dallimore, exited Founder, Angel Investor and Co-Founder & CEO of Continuous Software. In this conversation, Mark Dallimore shares his extensive experience in entrepreneurship, particularly in the project management software space. He discusses his journey through various startups, leading to the founding of Continuous Software and its flagship product, Engine. Mark emphasizes the importance of strategic planning, data utilization, and customer acquisition strategies in navigating the challenges of enterprise-level project management. He highlights the role of data in informed decision-making and the need for effective partnerships to facilitate customer onboarding and success. In this conversation, Mark Dallimore discusses the intricacies of navigating seed funding for startups, emphasizing the importance of aligning with like-minded investors and the challenges faced in the UK entrepreneurial landscape. He highlights the need for a supportive startup ecosystem and governmental incentives to foster innovation and retain talent. The discussion also touches on the cultural differences between the UK and US regarding entrepreneurship and the potential for growth in the tech sector. Takeaways - Mark's journey through various startups has shaped his approach to entrepreneurship. - Continuous Software was founded to address strategic planning challenges. - Aangine is designed to streamline project management for large enterprises. - Data plays a crucial role in making informed project decisions. - Customer acquisition should be paced according to business capacity. - Partnerships can ease the onboarding process for enterprise customers. - Planning is a discipline that can improve project delivery. - The software learns from historical data to optimize team assignments. - Effective communication of project status is essential for leadership. - The market for sophisticated planning solutions is vast and underexplored. The seed funding journey can take 18 months, requiring strategic pivots. - Aligning with investors who understand the startup's vision is crucial. - Team collaboration is essential for startup success. - Venture capitalists often seek clear KPIs and traction before investing. - Building relationships with angel investors can open doors to opportunities. - The UK startup ecosystem faces challenges that need addressing at a governmental level. - Entrepreneurs are increasingly seeking opportunities abroad due to unfavourable conditions at home. - The importance of creating a supportive environment for startups cannot be overstated. - Learning from successful startup ecosystems in other countries can provide valuable insights. - The entrepreneurial spirit in the UK needs revitalization to encourage innovation. Chapters 00:00 Foundational Experiences in Entrepreneurship 06:05 The Birth of Continuous Software 12:09 Understanding Engine: The Solution 17:47 The Role of Data in Project Management 23:56 Customer Acquisition Strategies 30:06 Navigating Enterprise Challenges 35:23 Navigating the Seed Funding Journey 39:00 Aligning with Like-Minded Investors 46:41 The State of Entrepreneurship in the UK 51:41 Building a Thriving Startup Ecosystem Follow Mark on LinkedIn here: https://www.linkedin.com/in/markdallimore/ Checkout Continuous Software here: https://wildvision.io/ Want a 1-hour free advisory session with the host Greg McCallum? Use the link on his LinkedIn profile.👇👇👇👇👇👇👇 https://meetings-eu1.hubspot.com/meetings/gmccallum?uuid=c7ed45d8-c8fe-4b6a-9eda-d062fd02c9ad

Welcome to Part One of our conversation with Mark Dallimore, co-founder and CRO of Continuous Software. In this part, Mark shares his extensive experience in the startup ecosystem and technology sector. He discusses the evolution of technology, the importance of innovation, and the challenges faced by startups. Mark emphasizes the significance of customer trust, grit, and determination in navigating the startup landscape. He also reflects on his personal journey into technology, highlighting how his background in music influenced his career path. In this conversation, Mark Dallimore discusses the intersection of music and technology, exploring how advancements in digital music have transformed the industry. He reflects on his journey from a musician to a tech entrepreneur, emphasizing the importance of data in modern business. The discussion also touches on the democratization of music production, the art of live performance, and the cultural experiences that shape our understanding of music. Mark introduces his startup, Engine, which aims to revolutionize data management and strategic planning for businesses. Takeaways - Mark Dallimore is passionate about solving technology problems. - Startups require a unique blend of grit and determination. - Customer trust is crucial for early-stage startups. - The technology landscape is constantly evolving and presents new opportunities. - Innovation often stems from identifying and addressing specific problems. - The journey of a startup is filled with challenges and learning experiences. - Building a product that resonates with customers is key to success. - Mark's background in music influenced his interest in technology. - The importance of adapting and pivoting in response to feedback. - Technology has transformed how we engage with the world around us. - --- The evolution of music technology has been significant since the 1980s. - Data has become a crucial element in every business. - The democratization of music production has allowed more creativity to flourish. - Live performances and DJing have transformed with technology. - Cultural experiences can deeply influence our appreciation of music. - Effective planning in business leads to better outcomes. - AI and machine learning are essential for modern data management. - Understanding human emotions is key in both music and business. - The music industry has shifted from physical to digital production. - Mark's startup, Engine, aims to streamline data management for organizations. Chapters 00:00 Introduction to Mark Dallimore and Continuous Software 03:05 The Evolution of Technology and Startups 06:08 The Impact of Technology on Society 08:52 The Journey of Startups and Building Solutions 12:12 The Role of Grit and Determination in Startups 15:01 Navigating Challenges in the Startup Ecosystem 17:46 The Importance of Customer Trust and Engagement 21:04 The Path to Innovation and Problem Solving 24:06 Mark's Personal Journey into Technology 26:38 The Evolution of Music and Technology 31:14 Democratization of Music Production 36:39 The Art of DJing and Live Performance 40:54 Cultural Experiences and Music's Impact 42:27 Introducing Engine: A New Era in Data Management Follow Mark on LinkedIn here: https://www.linkedin.com/in/markdallimore/ Checkout Continuous Software here: https://wildvision.io/ Want a 1-hour free advisory session with me, Greg McCallum? Use the link on my LinkedIn profile.👇👇👇👇👇👇👇 https://meetings-eu1.hubspot.com/meetings/gmccallum?uuid=c7ed45d8-c8fe-4b6a-9eda-d062fd02c9ad

Welcome to Part Two of our conversation with Xander. Watch Part One here: https://youtu.be/jvs7CnwKNng In this conversation, Gregory McCallum and Xander discuss the intricacies of business development, particularly for startups and tech companies. They explore the importance of persistence, listening, and providing value in business relationships. The discussion also delves into personal branding, influencer marketing, and the evolving landscape of content creation. Xander shares insights on building relationships in the creator economy and the significance of community and networking. The conversation emphasizes the balance between passion and discipline in pursuing business goals and the need for adaptability in content strategies. Takeaways -Be personable and adaptable in business development. -Persistence is crucial for success in reaching out. -Listening is key to understanding client needs. -Always provide more value than you take. -Sales should come before marketing for startups. -Building relationships is essential in business. -Personal branding is becoming increasingly important for founders. -Influencer marketing requires careful selection and due diligence. -Look for long-term partnerships with creators. -Adapt your content strategy to maintain engagement. Chapters 00:00 Navigating Business Development for Startups 02:57 The Importance of Listening and Value in Business 06:12 Understanding the Tech Startup Landscape 09:01 The Role of Personal Branding in Business 12:10 Influencer Marketing: Strategies and Pitfalls 14:58 Building Relationships in the Creator Economy 18:11 The Future of Content Creation and Business 20:57 The Evolution of Creators and Their Brands 24:02 Finding Balance: Passion vs. Discipline 27:03 The Importance of Community and Networking 29:51 Advice for Aspiring Content Creators Follow Xander on LinkedIn here: https://www.linkedin.com/in/xanderwilkins/ Checkout Wild Vision here: https://wildvision.io/ Want a 1-hour free advisory session with me, Greg McCallum? Use the link on my LinkedIn profile.👇👇👇👇👇👇👇 https://meetings-eu1.hubspot.com/meetings/gmccallum?uuid=c7ed45d8-c8fe-4b6a-9eda-d062fd02c9ad

In this conversation, Xander, head of business development at Wild Vision, shares his journey into the creator economy, discussing the evolution of content creation, the importance of community, and the challenges faced by investors in understanding this dynamic industry. He highlights the role of AI in content creation, the nuances between influencers and creators, and the impact of the adult industry on the creator landscape. The discussion also touches on the significance of community management and the future of AI influencers. Takeaways -Xander transitioned from sales to business development in the creator economy. -The creator economy is likened to a new form of Hollywood. -Community building is essential for content creators' success. -Investors often misunderstand the complexities of the creator economy. -AI is rapidly evolving and influencing content creation. -The adult industry plays a significant role in tech innovation. -Creators are increasingly viewing their work as a business. -OnlyFans is not just for adult content; it has broader applications. -Micro-influencers often have more engaged communities than macro-influencers. -Investment opportunities in the creator economy are growing. Chapters 00:00 - Introduction to the Creator Economy 03:00 - Xander's Journey into Business Development 06:04 - The Appeal of the Creator Economy 09:10 - Understanding Influencers vs. Creators 11:52 - Investment Challenges in the Creator Economy 14:53 - The Role of AI in Content Creation 17:54 - Community Building in the Creator Space 20:55 - The Future of AI Influencers 24:07 - Ethics and Anonymity in Content Creation 27:01 - The Impact of the Adult Industry on Content Creation 29:49 - Navigating the OnlyFans Landscape 32:52 - The Importance of Community Management 36:00 - Innovations in Community Engagement 39:04 - Conclusion and Future Discussions Follow Xander on LinkedIn here: https://www.linkedin.com/in/xanderwilkins/ Checkout Wild Vision here: https://wildvision.io/ Want a 1-hour free advisory session with me, Greg McCallum? Use the link on my LinkedIn profile.👇👇👇👇👇👇👇 https://meetings-eu1.hubspot.com/meetings/gmccallum?uuid=c7ed45d8-c8fe-4b6a-9eda-d062fd02c9ad

In Part Two of my conversation with Perdie and M from Hotbed we delve into the intricacies of the startup ecosystem, emphasizing the need for more in-depth discussions about entrepreneurship. We explore the challenges founders face, including the overwhelming amount of conflicting advice, the importance of authenticity, and the dynamics of investor relationships. The conversation also addresses mental health issues within the startup community, the impact of social media on founders, and the often-overlooked basics of starting a business. The episode wraps up with insights into the future of Hotbed and the importance of community support in the entrepreneurial journey. Takeaways -Founders need transparency in the investment process. -Investors often provide vague feedback, which is unhelpful for founders. -Authenticity is crucial in entrepreneurship; being a people pleaser is detrimental. -Mental health should be viewed as a health issue, not a personality flaw. -Social media platforms like LinkedIn can create pressure for validation. -The basics of starting a business are often overlooked in discussions. -Founders should focus on their unique journey rather than conforming to trends. -It's important to accept emotions as part of the human experience. -Conflicting advice can overwhelm founders; balance is key. -Hotbed aims to support founders through community and resources. Chapters 00:00 - The Need for Granular Conversations in Startups 03:14 - Navigating the Overwhelm of Startup Advice 06:12 - The Importance of Authenticity in Entrepreneurship 09:06 - Understanding Investor Dynamics 11:51 - The Future of Hotbed and Its Product 14:56 - Mental Health in the Startup Ecosystem 18:49 - The Impact of Social Media on Founders 22:06 - The Basics of Starting a Business 24:54 - Closing Thoughts and Future Directions Follow M on LinkedIn here: https://www.linkedin.com/in/margaretannecoyle/ Follow Perdie on LinkedIn here: https://www.linkedin.com/in/perdiealder/ Checkout Hotbed here: https://www.hotbed.co/ Want a 1-hour free advisory session with me, Greg McCallum? 👇👇👇👇👇👇👇 https://meetings-eu1.hubspot.com/meetings/gmccallum?uuid=c7ed45d8-c8fe-4b6a-9eda-d062fd02c9ad

In this conversation, the founders of Hotbed, M and Perdie, share their unique entrepreneurial journeys and discuss the evolution of Hotbed from its early roots at Tech Hub to becoming a virtual accelerator designed to support founders globally. They explore the challenges and opportunities they faced during the pandemic, the development of Hotbed’s revenue model, and the importance of community building in virtual settings. The conversation also dives into their personal backgrounds, the excitement of bringing ideas to life, and how generational differences shape attitudes towards career and risk. Hospitality and attention to detail play a crucial role in their approach to creating memorable experiences for startups. Takeaways -M and Perdie met at Tech Hub, which was pivotal for their careers. -Spice Startups evolved into Hotbed, focusing on virtual accelerator programs. -Hotbed supports founders globally, offering free resources and investor connections. -The revenue model relies on partnerships with companies targeting startups. -The pandemic prompted the creation of Hotbed as they faced job uncertainty. -Talent is globally distributed, but investment opportunities are not. -The excitement of entrepreneurship lies in bringing ideas to life. -Hotbed aims to support startups in navigating their growth challenges. -Community can be effectively built in virtual settings. -Attention to detail is crucial in creating memorable event experiences. -Generational differences impact attitudes towards career choices and risks. Chapters 00:00 - Introduction to the Founders 03:06 - The Journey to Hotbed 06:07 - Tech Hub Experience 08:54 - The Path to Entrepreneurship 12:01 - Childhood Influences on Entrepreneurship 15:00 - The Birth of Hotbed 18:01 - Navigating Challenges in Startups 22:06 - The Evolution of Spice Startups 25:09 - Understanding Hotbed: A Virtual Accelerator 28:10 - Revenue Models in Startup Support 31:01 - Addressing Global Investment Disparities 34:11 - The Role of Founders Camp 36:52 - Building Community in a Virtual World 40:07 - Creating a Unique Brand Experience 43:03 - The Importance of Detail in Events Follow M on LinkedIn here: https://www.linkedin.com/in/margaretannecoyle/ Follow Perdie on LinkedIn here: https://www.linkedin.com/in/perdiealder/ Checkout Hotbed here: https://www.hotbed.co/ Want a 1-hour free advisory session with me, Greg McCallum? Use the link on my LinkedIn profile.👇👇👇👇👇👇👇 https://meetings-eu1.hubspot.com/meetings/gmccallum?uuid=c7ed45d8-c8fe-4b6a-9eda-d062fd02c9ad

Welcome to Part Two of my conversation with Sam Oliver. Here we discuss the complexities of building software, particularly in the financial sector, and the potential of AI in automating sales processes. He emphasizes the importance of customer engagement and the evolution of conversational AI, while also addressing ethical considerations and the balance between innovation and regulation. Sam shares his personal ambitions and thoughts on the future of his career, highlighting the significance of health and well-being amidst professional pursuits. Takeaways - Building software is inherently complex and challenging. - AI has the potential to revolutionize sales automation. - Customer engagement can be significantly enhanced through AI. - Conversational AI will play a crucial role in future business interactions. - Ethics and governance in AI are becoming increasingly important. - Innovation must be balanced with regulatory considerations. - Personal health and well-being are essential for sustained success. - Networking opportunities are greater in startup hubs like San Francisco. - The future of AI may involve more manipulative technologies. - Investing in startups requires careful consideration and alignment with personal values. Chapters 00:00 - Navigating Complexity in Software Development 02:36 - The Role of AI in Sales Automation 06:01 - Enhancing Customer Engagement with AI 09:47 - The Future of Conversational AI 14:30 - Ethics and Governance in AI 20:19 - The Balance of Innovation and Regulation 27:33 - Personal Ambitions and Future Goals Follow Sam here: https://www.linkedin.com/in/sam0liver/ Check out OpenFi here: https://www.openfi.tech/ Want a 1-hour free advisory session with me, Greg McCallum? Use the link on my LinkedIn profile.👇👇👇👇👇👇👇 https://meetings-eu1.hubspot.com/meetings/gmccallum?uuid=c7ed45d8-c8fe-4b6a-9eda-d062fd02c9ad

In Part One of my conversation with Sam Oliver, he shares his entrepreneurial journey, detailing his experiences from starting his first startup at age 20 to his current venture, OpenFi, which aims to revolutionize the sales development process using AI. He discusses the importance of customer experience, the challenges faced during the acquisition of his previous company, and the legal hurdles that followed. Sam emphasizes the lessons learned throughout his journey, particularly regarding sales strategies, customer fit, and the significance of pre-qualification in the sales process. Takeaways - Sam started his first startup company at age 20. - OpenFi automates the sales development representative role using AI. - Customer experience is significantly improved with AI solutions. - Eden Property serves as Sam's retirement business. - Sam transitioned to tech entrepreneurship due to the rise of social media. - Exiting his previous company was always part of his plan. - Legal challenges can arise unexpectedly during an acquisition. - Possession is nine-tenths of the law in legal disputes. - Revenue growth is crucial for startup success. - Understanding customer needs is essential for effective sales strategies. Chapters 00:00 - Introduction to Sam Oliver 02:54 - The Journey of Entrepreneurship 06:03 - OpenFi: Revolutionizing Sales Development 09:00 - Customer Experience and Technology 12:04 - Eden Property: A Business Overview 14:58 - The Transition to Tech Entrepreneurship 17:58 - The Acquisition Experience 21:57 - Navigating Legal Challenges 26:09 - Lessons Learned from the Acquisition 29:52 - Sales Strategies and Customer Fit 33:01 - The Importance of Pre-Qualification 36:01 - Final Thoughts and Reflections Stay tuned for Part Two! Follow Sam here: https://www.linkedin.com/in/sam0liver/ Check out OpenFi here: https://www.openfi.tech/ Want a 1-hour free advisory session with me, Greg McCallum? Use the link on my LinkedIn profile.👇👇👇👇👇👇👇 https://meetings-eu1.hubspot.com/meetings/gmccallum?uuid=c7ed45d8-c8fe-4b6a-9eda-d062fd02c9ad