How to Create a Great Incentive Structure for Your Team (James Dooley Interviews Mads Singers)
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What Does “How to Create a Great Incentive Structure for Your Team (James Dooley Interviews Mads Singers)” Talk About?
This episode of the James Dooley Podcast features a conversation between James Dooley and Mads Singers focused on how to build effective incentive structures for teams, particularly for small business owners and entrepreneurs. The discussion opens with a strong warning against giving away equity too early, with both hosts agreeing that founders often undervalue their businesses and hand over significant ownership before truly knowing whether a hire will deliver. Mads explains why equity frequently fails as a motivator, noting that some employees have even handed equity back because it held no real meaning for them.
The conversation moves into practical alternatives to equity, including profit sharing tied to company growth milestones, team-based bonuses that reward collective performance, and commission structures for sales-focused roles. Mads and James also explore a wide range of non-financial incentives such as health insurance, extra holidays, four-day work weeks, gym memberships, and personalised rewards like weekend experiences. A notable point raised is the value of practical support for remote teams, including paying for Starlink internet in the Philippines to improve both quality of life and productivity.
Throughout the episode, both speakers emphasise that effective incentives require understanding individuals rather than applying a one-size-fits-all approach. Mads highlights the value of personality profiling in identifying what actually motivates different team members, noting that doubling a salary does not automatically produce greater effort. The episode concludes with an invitation for viewers to share their own experiences with incentive structures across both in-house and remote teams.
“Business owners often see equity as the ultimate motivator, but for most people it really is not. Owning ten percent of something that has no clear value does not motivate most employees.”
— Mads Singers
Who Are the Guests on “How to Create a Great Incentive Structure for Your Team (James Dooley Interviews Mads Singers)”?
Mads Singers is a management consultant and entrepreneur with extensive experience advising small business owners and founders on team building, remote staffing, and incentive design. He is particularly well known for his work with remote teams in Southeast Asia and his use of personality profiling to help business leaders understand and motivate their staff more effectively. Throughout the episode, Mads draws on real-world examples from his consulting work to illustrate why common incentive approaches often fail and what founders should do instead.
James Dooley is a serial entrepreneur and digital business builder who hosts the James Dooley Podcast. He brings a grounded perspective shaped by his own experience managing teams across multiple businesses. In this episode, James contributes his personal rule of requiring at least three years before considering equity for any team member, and shares his broader philosophy that trust must be tested through both good times and difficult periods before meaningful ownership is offered.
What Are the Key Takeaways From “How to Create a Great Incentive Structure for Your Team (James Dooley Interviews Mads Singers)”?
Here are the key points discussed in this episode:
- Equity should not be offered to new hires until they have demonstrated consistent delivery and become a genuinely critical part of the business over an extended period, with both hosts suggesting three years as a practical minimum.
- Equity is far less motivating to most employees than founders assume, and some staff have even returned equity because it held no real value for them in the absence of a clear company valuation.
- Profit sharing tied to specific growth targets, such as revenue increasing from one million to three million, offers a powerful alternative to equity by creating tangible upside linked directly to company performance.
- Non-financial and personalised incentives such as health insurance, upgraded home office equipment, additional leave, and experience-based rewards can be more effective motivators than salary increases alone.
- Understanding what actually motivates each individual team member, through tools like personality profiling, is essential because different people respond to entirely different incentives and there is no single solution that works for everyone.
“You can double someone's salary and still get no extra effort from them.”
— Mads Singers
Is “How to Create a Great Incentive Structure for Your Team (James Dooley Interviews Mads Singers)” Worth Listening To?
This episode is worth listening to because it cuts through the idealised thinking that often surrounds equity and incentives and replaces it with practical, experience-backed guidance. Rather than offering abstract theory, Mads Singers uses specific examples, including staff handing back equity and the impact of paying for Starlink for remote workers in the Philippines, to illustrate points that founders can immediately apply to their own businesses. The conversation is candid and covers both the financial and human dimensions of keeping great people engaged.
What makes this episode particularly valuable is the way it challenges assumptions that many founders hold without questioning them. The idea that equity is the ultimate motivator is examined and largely dismantled, while the discussion of personalised and non-financial incentives opens up a much broader toolkit for business owners. Whether you are managing a small in-house team or a distributed remote workforce, the frameworks and examples shared here offer a clearer, more honest picture of what actually drives performance and loyalty.
Who Should Listen to “How to Create a Great Incentive Structure for Your Team (James Dooley Interviews Mads Singers)”?
This episode is ideal for:
- Small business owners and entrepreneurs who are building their first teams and considering how to structure compensation and ownership
- Founders managing remote or offshore teams who want practical strategies for retaining staff and improving performance without relying on equity
- Operations managers and senior leaders responsible for designing incentive programmes that align team behaviour with company goals
- Entrepreneurs who have already made mistakes with equity or bonus structures and are looking for a more grounded approach to rebuilding team incentives
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What Are Listeners Saying About This Episode?
“The section on why equity rarely motivates employees was genuinely eye-opening. Mads makes a compelling case with real examples, including staff actually handing equity back, which I had never considered before. This episode changed how I am thinking about our next senior hire.”
“I appreciated how specific the advice was. The example about paying for Starlink for remote workers in the Philippines as a low-cost, high-impact incentive is exactly the kind of practical insight I come to podcasts for. Short episode but packed with value.”
“James and Mads clearly have real experience to draw on and it shows throughout. The three-year rule for equity and the point about testing trust through both good and bad times resonated with me after going through a difficult period with a key team member. Highly recommended for any founder building a team.”
James Dooley: Hi, today I’m joined with Mads Singers, and today’s episode is about how to create a great incentive structure for your team. Mads Singers: Incentive structure is one of the questions I get most often, particularly from small business owners and entrepreneurs. They are usually very eager to give away their business before they have even built one. My general approach is do not do that too early. I see a lot of people make the mistake of hiring someone and giving them equity straight away. They might have a small company with four, five, or ten people, and they want to hire a great marketing person. They go out and say, “Here is a salary plus equity.” My philosophy is simple. I would never give equity until I see that the person can deliver. The reason is simple. So many people have brought someone in, given them equity, and then discovered that the person was a complete failure. If you give someone equity early, getting rid of them later can be extremely painful, depending on how the contracts are set up. When it comes to equity, I always recommend waiting longer. Make sure people are fully bought in. Make sure they are delivering. I have mainly done this in situations where someone becomes a critical part of the business. That could be an operations manager, a senior marketer, or a salesperson. These are people who become so ingrained in the business that you simply do not want to lose them. James Dooley: I completely agree. For me, incentives are tied to certain goals, and part of that goal is time. I do not believe you can fully trust someone until you have worked with them through both good and bad times. It is easy to trust people during growth periods, but when times get tough, you really see how people react. Until I have experienced that with someone, I would never consider equity. For the businesses I am involved in, three years is the minimum. I would never give equity in a business that I know will have a specific value further down the line until someone has proven themselves over time. I think too many founders fail to value their business properly. If you are good at what you do and have a clear plan, you can raise capital without giving away huge chunks of equity. I see horror stories all the time where people give away 10, 20, or 30 percent far too early. What are your thoughts on timelines? I use three years as a rule of thumb, even though I know it depends. Mads Singers: I have never had a fixed timeline in mind, but thinking about it now, I have never given equity in less than three years either. I want to see consistency over a long period. I want to see ownership and responsibility. I want to see growth. That shows me the person is not just a one trick pony. Another important point is that business owners often see equity as the ultimate motivator, but for most people it really is not. Owning ten percent of something that has no clear value does not motivate most employees. I have worked with companies where staff literally handed equity back and said they did not care about it. That shows how little it meant to them. For me, incentive structures are about creating upside without relying on equity. People should benefit when the company does well. With sales teams, commission makes sense. Outside of sales, I do not believe in paying bonuses when the company is losing money. I prefer team based incentives. If the company hits certain growth targets, then the senior team benefits together. For example, if revenue grows from one million to three million, you might take two hundred thousand and divide it across the team. The key is setting clear goals with tangible outcomes. James Dooley: We have talked about equity and profit sharing, but there are many other incentives. I want to list a few and get your thoughts. Health insurance is a big one, especially for overseas teams. Extra holidays, bank holidays, or additional annual leave. Some people value time off more than pay rises. Others prefer a four day work week. Some companies offer gym memberships, team events, or trips. What have you found works best? Mads Singers: I like all of those, and this is where personality profiling is extremely valuable because different people are motivated by different things. Most entrepreneurs are motivated by money, but most employees are not. You can double someone’s salary and still get no extra effort from them. We focus a lot on practical incentives. For example, internet quality is huge for remote teams. When Starlink became available in the Philippines, we paid for it for some team members. It was a small cost for us but made a massive difference to them and to productivity. Health insurance is another strong incentive. We have also bought desks, chairs, monitors, and other equipment when we knew it would improve someone’s work life. We have done experiences as well, like weekends away with a partner as a reward. There are many incentives beyond money. For some teams, financial incentives still matter, especially commission based roles, but there is no single solution. The key is understanding the individual. James Dooley: Anyone watching this, let us know what incentives you have used, whether for in house or remote staff. What worked well? What did not work well? Mads, it has been an absolute pleasure having you on. Thank you very much.
Creators & Guests
Host
James Dooley is a UK entrepreneur.