Exiting a business is one of the biggest milestones for any founder, entrepreneur or family business owner. After years of hard work, reaching that finish line brings a mix of relief, pride, and—quite often—uncertainty. You may find yourself at a crossroads, asking: What’s next?
For many, the natural next step is to explore roles as an investor, Non-Executive Director (NED), or perhaps start something entirely new. But the decision isn’t always straightforward. Having gone through this journey myself, I can tell you that while these options are appealing, they come with their own set of challenges.
When I exited my previous business, I knew exactly what I didn’t want. I didn’t want to simply sit on the sidelines as an investor. I wanted to be in the room when key decisions were made, to use my experience to shape the future of the companies I worked with. That’s how TWYD & Co was born, and it’s been one of the most rewarding decisions of my career. However, this journey has taught me a few lessons, which may resonate with you if you’re considering your next move.
Angel Investing: A Limited Role?
Angel investing can be an exciting venture after an exit, allowing you to back up-and-coming companies. Yet Entrepreneurs are used to being at the heart of things, and angel investing often means being one of many with little room to actively shape the business’s direction.
For many of us, writing a cheque simply isn’t enough.
While it’s fulfilling to support innovation, many of us want more than just a financial stake—we want a seat at the table where our voice can influence the company’s future. That’s why angel investing alone can feel like a halfway step, especially for those of us who thrive on being deeply involved.
Direct Investments: Where Experience Meets Opportunity
Direct investments offer a chance to use your entrepreneurial skills in a more hands-on way. By investing in industries you know well, you can bring far more than capital to the table—you bring expertise, strategy, and the kind of insight that only comes from having been in the trenches.
These investments strike a balance. You can take an active role, helping to drive growth and key decisions, but without the full-time pressure of running the company. It’s an ideal middle ground for entrepreneurs who want to make an impact, but aren’t necessarily looking to dive back into the CEO role.
NED Roles: Diversification with Challenges
Building a portfolio of NED roles can be an attractive way to diversify your career after an exit. It allows you to work across various sectors, helping businesses at a board level with strategy, governance, and growth. However, finding the right fit can be tricky.
Not every company offers the level of involvement we might seek. Entrepreneurs are used to having control, making decisions, and driving strategy. In a NED role, your influence can be more limited, depending on the company’s governance structure and how much they value your input. The key is finding companies where your expertise is both needed and appreciated.
Giving Back: Philanthropy and Social Impact
For many entrepreneurs, a business exit presents a unique opportunity to give back in a meaningful way. After years of focusing on growth and profitability, the post-exit phase offers the chance to contribute to causes that resonate with your personal values and passions.
Philanthropy can take many forms—whether it’s creating a charitable foundation, supporting social enterprises, or using your skills and experience to mentor the next generation of entrepreneurs. Giving back not only allows you to make a positive impact, but it also provides a sense of purpose and fulfilment that’s often hard to replicate in other business ventures.
Many find that aligning their philanthropic efforts with their previous industry expertise offers a way to stay connected to the business world while making a tangible difference. Whether you choose to focus on education, sustainability, or community development, philanthropy can offer a new sense of direction and a legacy that extends beyond financial success.
Starting Something New: Backing Yourself
Sometimes, the best next step is to back your own knowledge and experience. That’s exactly what I did with TWYD & Co, and it’s been one of the most fulfilling decisions of my career. Starting a new venture after a business exit allows you to take everything you’ve learned—both your successes and failures—and apply it with fresh perspective.
Of course, it’s not easy. Building something from the ground up requires energy, focus, and a strong sense of determination. But for entrepreneurs, this is often when we feel most alive. We know the journey, and we have the skills to navigate its twists and turns.
The Importance of Relationships
No matter which path you choose—whether it’s investing, taking on NED roles, starting your own venture, or getting involved in philanthropy—there’s one thing that’s absolutely crucial: relationships.
Finding the right opportunities isn’t about luck.
It’s about networking, building connections, and identifying companies or individuals where you can add real value. It’s not just about financial investment—it’s about bringing something deeper to the table: your experience, your insights, and your ability to drive change.
For those at a post-exit crossroads, the journey ahead is full of potential. The key is to seek out opportunities where your experience can shape more than just financial returns—where you can have a real, lasting impact.
About the Author:
David Twiddle is an entrepreneur who has founded two separate businesses and led both through to successful exit. As Founder and Managing Partner of TWYD & Co, David now advises founders, entrepreneurs, and family businesses on executive appointments and complex, sensitive people-related challenges often found in private enterprises. Contact David at dt@twyd.co