Explore Howard Blake’s journey from selling shirts out of his car to building successful companies across four continents. In this episode of The Freedom Experience, we dive into bootstrapping, hiring A-players, and servant leadership, and how focus and core values drive lasting success.
Read time: 7.37 minutes.
Read this on: jeanmoncrieff.com
What's in store for today:
- Why bootstrapping beats venture capital
- How to hire and hold onto A-players
- The power of servant leadership
Hey there,
Howard Blake is the kind of entrepreneur whose story makes you stop and wonder what it truly takes to succeed.
He’s built over 20 companies across four continents—but he didn’t start out with investors, a strategic plan, or a groundbreaking product.
He started by selling shirts out of the trunk of his car.
From that humble beginning, Howard grew businesses in industries as diverse as call centers and predictive software for finance and real estate, all through the power of resilience and resourcefulness.
In this episode of The Freedom Experience®, Howard shares his journey—the wins, the setbacks, and the lessons learned from building successful businesses without a safety net.
We explore how the challenges of bootstrapping taught him the value of agility, how he learned to scale while staying lean, and why staying close to your customers is the best strategic move you can make.
His story isn’t just about business growth; it’s about personal growth, pushing past limits, and refusing to let setbacks define you.
Whether you’re an established business owner or just starting out, Howard’s journey is packed with insights into what it means to create, adapt, and grow.
Get ready for an inspiring conversation that dives deep into the real work of entrepreneurship—the kind you don’t often see, but that shapes every successful venture.
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1. Why Bootstrapping Beats Venture Capital
One key takeaway from Howard's journey is the power of bootstrapping over pursuing venture capital.
Most companies I work with are established, generating solid revenue, and have grown with little or no outside investment.
The owner retains full control of the business’s destiny.
As an investor, I’m drawn to these kinds of businesses. They may not be perfect, but they’ve built a working engine—one that can be fine-tuned and optimized for greater efficiency.
Bootstrapping forces efficiency and resourcefulness. When your money is on the line, every decision counts and waste is minimized.
This is where bootstrapping differs.
Venture-backed startups often have a “runway mentality”—we have X days, weeks, or months of cash left, then we need to raise more.
This approach can stifle creative problem-solving and the pursuit of a sustainable business model. The focus is more on raising the next round than on figuring out a viable business model.
Then there is the talk about "founder-led sales," but how is that different from bootstrapping?
It’s just a way to ensure the business is generating revenue. If you're already bringing in revenue, it’s worth asking why you’re seeking investment in the first place.
Does your need for investment line up with a much bigger vision?
If you're thinking of going the VC route, pause for a moment and take a critical look at your business. Do you really need an outside investor? Or can you bootstrap the sucker?
Bootstrapping? here are 5 things you must get right:
- Clarity of vision: Know exactly where your company is headed (you'll need to sell this to a VC anyway, so get clarity early).
- Core customer focus: Ensure you have a customer who truly values your product.
- Cash flow system: Create a system that consistently puts money in the bank. Cash fuels growth!
- The right team: A handful of A-players are worth more than an army of Bs and Cs.
- Start small: Stay on track and avoid distractions—don’t try to boil the ocean, chase shiny objects, or go down rabbit holes.
Take a listen to Andrew Butt discussing the importance of not "boiling the ocean" when you're starting out. One of the things I noticed while working with Andrew was his ability to balance a big vision with a strong focus on what he calls "the most valuable use case."
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Sure, Andrew took funding and ultimately created a unicorn, but in the early days, he focused on building a viable business first. Only then did he seek investment to scale his vision aggressively.
Before chasing VC funding, consider the benefits of growing at your own pace. Bootstrapping isn’t easy, but it builds a more adaptable, grounded, and ultimately successful business.
2. How to hire and hold onto A-players
What is an A-player?
An A-Player is someone you bring into your business who not only has the experience, skills, and ability to excel but also aligns closely with your core values.
It's not just about exceeding expectations—it's about embracing values.
To build a high-performing team, you need a majority of A-players.
Do not tolerate mediocrity.
Too often, businesses hire just to fill a gap, settling for "good enough" because they need someone now. This is a costly mistake. Rushing the recruitment process can set your business back months. Instead, focus on finding people who truly fit.
A-Players want to be part of a winning team. They thrive on accountability, seek opportunities, have the skills to succeed, and desire coaching to grow.
Finding A-Players starts at the top...
A company with a compelling vision, strong leadership, and a culture of A-players is far more likely to attract top talent.
As CEO, your role goes beyond execution, cash flow, and strategy—it’s about finding the best people and building a high-performing team.
Your talent must align with your vision and strategy. When you create your org chart, you need to consider how to fill each role with an individual who has the skills and values that align with your strategy.
Focus on...
- Core Values Alignment: Ensure they truly share your company’s values.
- Unique Capability: Seek out skills that fit your company’s strategy.
- Accountability: Assign ownership of critical functions to individuals who will exceed expectations.
How to attract and recruit A-Players...
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Rigorous Interviews: Use structured processes like Top Grading - read Foolproof Hiring by Brad Smart & Chris Mursau.
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Competitive Compensation: Pay well, including options or equity where possible.
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Effective Onboarding: Set them up for success from day one - read Onboarded by Brad Giles.
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Consistent Metrics: Create scorecards before you recruit, through the interview process (set expectations), and later, to track performance.
How to keep A-Players...
- Provide development opportunities: A-players thrive on continuous learning, and leaders need to grow in pace with the business growth.
- Offer clear growth pathways: As your business scales, ensure employees have opportunities to grow and advance. Growth is so important, and top talent leaves when growth stalls.
- Continuous coaching: A-players seek regular feedback and development to stay engaged and perform at their best.
Need Help Building Your A-Team?
If you're struggling to find or keep A-Players, or if you're ready to break free from growth stagnation, we can help. Join one of our upcoming Foundation for Growth Masterclasses.
Together, we’ll dive into how to overcome these challenges, evolve your leadership team, and drive long-term, sustainable growth.
Join our upcoming Foundations for Growth Masterclasses 👇
3. The power of servant leadership
When I visited Wasserle, I walked away with more than just insights—I took away powerful lessons that every business owner can learn from.
Markus Wasserle owns two unique businesses outside of Munich. One provides cleaning services to some of Munich's biggest corporations, and the other is a climbing gym with the kind of cuisine you'd expect from a Michelin-starred restaurant.
But what truly struck me wasn't just the diversity of Markus's ventures—it was how he embodies servant leadership in everything he does.
His businesses are built to serve his family, community, customers, and employees with unwavering dedication.
How many companies do you know that provide a concierge service for employees who call in sick, sending a standby team straight to clients so nothing is missed? Or celebrate each employee's birthday with a personal gift—for over 400 people—and arrange everything from international trips to funerals?
These are just a few of the reasons why Wasserle has one of the lowest absentee rates in the industry.
Markus is also intentional about his core customers.
In the cleaning business, their ideal client is property owners because their value proposition is to increase the value of the buildings they serve.
They understand that giving a building that extra sparkle directly impacts the property's value.
For the climbing gym, families are at the heart of everything they do.
Kids often influence the decisions on where families spend time together, so the gym's offerings are geared toward making it a family destination.
It's open from 7 AM to 10 PM, seven days a week, because they don't want customers to wonder if operating hours vary from day to day.
Perhaps the most intriguing part of the climbing gym is that Markus created it as part of his recruitment strategy.
Not many people think about going into the cleaning business, but the climbing gym allows Markus to connect with the community and attract people to his business.
Markus’ intense focus on serving his core customer—whether it's a property owner or a young family—is something many less successful companies struggle with.
They hesitate, afraid they'll miss opportunities by narrowing their focus. But Markus knows that by clearly defining his core customer, he can serve them better than anyone else.
He hasn't lost customers from outside his core focus; instead, he's created an experience that truly stands out.
This is the power of knowing—and serving—your community, employees, and your core customer.
One quote to start the week strong
"Success isn't always about greatness. It's about consistency. Consistent hard work leads to success. Greatness will come.- Dwayne Johnson
Consistency is often the missing ingredient in business success, especially in areas like marketing.
As business owners, we can get caught up in chasing the latest trends or jumping from one idea to the next, hoping for a quick win.
But true success comes from showing up consistently, even when progress seems slow.
It's the cumulative effect of sustained effort that drives real results.
So stay focused, adjust when needed, but avoid constantly switching tactics. Consistency wins the long game.
Have a great week!
- Jean
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