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A Design Thinking Approach to Investing & Early retirement.
Most people work for decades without ever calculating whether they are actually on track for retirement.
After selling my own company, I spent five years studying investing, testing strategies, and building tools to understand how financial decisions shape our future.
That journey eventually led me to create Plan B Investing — a framework and simulator designed to help professionals design their financial future with clarity and confidence.
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Hi, I'm Jan Kennedy
British-German entrepreneur and investor living the FIRE dream. Built a multi-million training company from the ground up, sold it, then helped scale a start-up to 1,000+ employees and a public listing. Oh, and my accelerator trainings? They've been trusted by 2,000+ entrepreneurs and Fortune 500 innovators to turn their business ideas into reality.
I've dabbled in just about every investment playground—funds, property, start-ups, stocks, and crypto. Hit financial freedom before 40 (yes, really!), and now I'm on a mission through Plan B Academy to help others do the same. Whether you're building your first investment portfolio or planning your dream retirement, I'm here to share the playbook that actually works.
contact@planbinvesting.me
From Corporate Career to Entrepreneur
Like many people, my career started on a fairly traditional path.
I joined a fast-growing startup called Meltwater, where I worked in sales and later management during the company's early expansion. It was an intense and exciting environment — building teams, hitting ambitious targets, and helping scale a global business.
During those years I learned a lot about growth, strategy, and performance.
But something slowly became clear to me.
Even in successful companies, most people were still trading time for money. The rewards were good, but the path ahead often looked predictable: work hard for decades and eventually retire.
I began to wonder:
Is this really the only financial trajectory available to most professionals?
That question stayed with me.
Building and Selling My Own Company
Eventually I decided to test a different path.
I left the corporate world and started my own business focused on innovation and corporate entrepreneurship. My work involved helping companies design new ventures, launch products, and think more creatively about growth by applying the lean startup methodology and business model canvas.
Over the years I had the opportunity to work with many organizations and mentor thousands of innovators and entrepreneurs.
It was an incredible learning experience.
And eventually, the business grew to the point where I was able to sell the company.
Suddenly I found myself in a very different position.
For the first time, I had both time and capital to ask deeper questions about the future.
“Most people spend more time planning their next holiday than planning their financial future.”
Five Years Studying Investing and Financial Independence
After selling the company, I went down a rabbit hole.
For nearly five years, I immersed myself in learning about investing, financial independence, and long-term wealth building.
I read dozens of investing books, studied countless strategies, listened to hundreds of podcasts, and tested many different approaches.
Stocks. Crypto. Real estate. Alternative assets. Portfolio construction. Tax strategies. etc.
At the same time, my life outside investing was evolving too.
My wife and I were growing our family, raising young children, and thinking about what kind of future lifestyle we wanted to design.
That combination — investing experimentation and real-life decisions — led me to a powerful realization:
Most financial advice doesn't help people connect investing decisions with real life outcomes.
People are told to save and invest… but rarely shown how those decisions actually shape their future.
The Problem I Kept Seeing
As I spoke with friends, colleagues, and professionals around me, I noticed something surprising.
Many successful people were still unsure about their long-term financial trajectory.
Questions kept coming up:
- When could they realistically retire?
- Were they saving enough?
- Should they invest more aggressively?
- Could they afford to change careers or start a business?
- What impact would different choices have on their future?
Most people were navigating these questions without a clear framework.
They were making decisions based on guesses, fragmented advice, or generic retirement calculators that assumed unrealistic investment paths.
I realized that what many people needed wasn't just investment tips.
They needed a way to prototype their future.
A system to test different financial scenarios and understand the consequences of their choices.
Why I Created Plan B Investing
That idea eventually led me to create Plan B Investing.
Plan B is built around a simple philosophy:
Your financial future should be something you design intentionally, not something you discover by accident decades later.
Through the Plan B Simulator and programs, my goal is to help professionals:
• understand their current financial trajectory
• explore different retirement scenarios
• identify the key levers that influence financial freedom
• and build confidence in their long-term strategy
One of the most surprising things people discover is that relatively small adjustments — saving slightly more, improving investment returns, optimizing taxes, or adjusting lifestyle expectations — can shift retirement timelines by 10, 15, or even 20 years.
Clarity changes everything.
And once people can see the path ahead more clearly, they begin making decisions with far greater confidence.
3 Lessons I Learned the Hard Way About Investing
Over the years I’ve experimented with many different investing strategies. Some worked well. Others taught me valuable lessons.
Here are three insights that fundamentally changed how I think about investing and financial planning.
1. Most People Don’t Know Their Financial Trajectory
One of the most surprising discoveries I made was how few people have ever calculated their long-term financial trajectory.
Even highly educated professionals often know:
• how much they earn
• how much they save
• roughly what they have invested
But they rarely know the answer to the most important question:
Where does this actually lead?
Without modelling the future, it’s impossible to know whether your current path leads to financial security — or financial stress later in life.
That realization is what ultimately led me to build the Plan B Simulator, so people could see how different decisions change their long-term outcomes.
2. Small Decisions Compound More Than People Expect
When I started experimenting with financial models, something became clear very quickly.
Small changes compound dramatically over time. For example:
• increasing your savings rate
• improving investment returns
• reducing taxes
• adjusting retirement lifestyle costs
Each of these decisions might look small in isolation.
But over 20–30 years, the combined impact can shift retirement timelines by 10, 15, or even 20 years.Once you see those dynamics clearly, financial planning becomes far less abstract.
You begin to understand which decisions actually matter.
3. Confidence Comes From Clarity
Perhaps the most important lesson I learned is that financial confidence doesn’t come from following the latest investment trend. It comes from understanding your own financial system.
When people can clearly see:
• their future investment trajectory
• the impact of different financial decisions
• the trade-offs between lifestyle and savings
they start making decisions with far greater confidence.
Instead of reacting to uncertainty, they begin designing their financial future intentionally.
That mindset shift is exactly what Plan B Investing is designed to support.
If you’ve ever wondered:
• Am I on track financially?
• When could I realistically retire?
• What happens if I invest more or change my strategy?
• Could I reach financial independence earlier than expected?
Then the best place to start is by running your own simulation.
Start designing your own exit plan - Plan B
See your retirement trajectory
The Plan B Simulator allows you to explore different financial scenarios and see how your decisions today shape your future.
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Optimise Your Retirement Game Plan:
A Practical Guide To Creating An Achievable And Sustainable Action Plan
Find out how entrepreneur turned investor reached the FIRE dream and how you can do it too - whether you hold an 9-5 job, a business owner, or have had a successful career for the past 20-30 years, can take this vital step to audit your financial health and to secure the financial future.
My Philosophy
Over the years I’ve become convinced of a few important principles:
1. Financial freedom is largely a design problem.
Most people never model their financial future — they simply react to it.
2. Small decisions compound massively.
Savings rate, investment returns, tax efficiency, and lifestyle choices can move retirement timelines by 10–20 years.
3. Clarity creates confidence.
When people can see the financial trajectory ahead of them, they make better decisions.
Plan B was built to give people that clarity.
See you on the Inside
Jan
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