Madis Pajo Coaching

Clear moves in investments, business, leadership and sales. 

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Madis has a natural strength of seeing what’s possible — and then giving you the courage and tools to make it real.

He helps ambitious people make confident, strategic decisions in:

investments

business building

leadership and team growth

No theory. No hype.

Just 20 years of real-world experience turned into clear structure and action.

How I Can Help

1. Build Financial Freedom

Investment Coaching — From Savings to Strategy

For you if:

  • You already have a financial base: at least ~€100K in savings, investments, or business assets.
  • Your money is “somewhere” (account, real estate, one type of investment), but there is no clear long-term strategy.
  • You want to grow your capital, but you’re stuck between fear of risk and fear of missing out.
  • You read and “know” a lot… but actual investment decisions happen rarely or randomly.


What Madis helps you with:

  • A clear overview of your current assets, risks, and opportunities.
  • A personal wealth strategy aligned with your time horizon, goals, and risk profile.
  • Concrete next moves: which assets to build, reduce, or add — and in what order.
  • Decision frameworks so you don’t freeze at every market movement.
  • An investor’s mindset: thinking in capital, leverage, scalability, and long-term value.

Result:

You move from “I should invest better” to a simple, written plan and real positions taken.
Less emotional guessing. More confident, long-term growth.

2. Idea to Execution

Entrepreneur Coaching — Make Your Business Real

For you if:

  • You’re ready to move from a stable job into your own business.
  • Or you already have a business, but growth feels messy and reactive.
  • Your ideas are strong, but you lack structure: offers, numbers, processes.
  • You don’t want to waste 3–5 years “trying things” without a clear roadmap.


Typical starting points:

  • “I have a business idea, but I don’t know if it’s financially sound.”
  • “My revenue is inconsistent. I need a clear plan and stability.”
  • “I haven’t built a business, I have built a job for myself. I want more freedom..”


What Madis helps you with:

  • Clarity on your business model, target client, and value proposition.
  • A practical, financially grounded business plan: pricing, costs, margins, cash flow.
  • A simple execution rhythm: what to focus on weekly and monthly.
  • Systems for sales, team, and financial discipline.
  • A thinking partner for the ups and downs so you don’t spiral or stall.


Result:

Your idea becomes a working, earning business with clear priorities.
You stop building randomly and start growing with structure.

3. Getting Results Through People

Leadership & Performance Coaching

For you if:

  • You’re a founder, manager, or sales leader who now needs results through others, not just your own effort.

  • Your team is good, but the standards could be better

  • You struggle to attract talent or keep talent.

  • You want to grow your leadership level


Result:

A scalable team: clearer goals, more ownership, better results — with less daily firefighting from you.

  1. Graduated with a business degree (BSc in Business Administration, TalTech, MSc under-graduate, EBS); yet a continuous learner through countless books, seminars, 1:1 conversations etc about the topics of investing, business building, scaling, personal productivity and world-class leadership.
  2. During university years was one of the first ones to start selling and building a team for LHV pension funds.
  3. At the age of 22, co-founded Sellit Group, designing corporate sales systems and training programs for brands like SEB, Sportland, Starman, DenimDream and Sangar, improving performance across teams.
  4. 18 years of entrepreneurship and leadership: deep dives into investing in real estate, start-ups, agriculture, sales mastery, recruiting A+ players and coaching top talent.
  5. Trained and led hundreds of salespeople internationally through the U.S.-based Southwestern Advantage, growing new leaders in Estonia, Poland and Slovakia.
  6. Navigated and led through global disruption (COVID-19) — successfully restructured the business from U.S. operations to the U.K., maintaining unity and performance despite a total visa ban.
  7. Recognised for being a top salesperson year after year, ranking among the top 100 sales people ever among 200 000 sales people (Mort Club, Diamond Growth, Platinum Level Sales and Leadership).
  8. Personally built and coached the #1 team in the international ranking among US and European teams.
  9. Invested in 20+ start-ups and helped raise crucial capital for some of those (Bolt, Sunly, Atom Mobility, eAgronom, Iconfit, Silen etc)
  10. Building personal financial freedom through investing since 2006. 50% club.
  11. Was a founding partner in building a 50+ unit real estate portfolio of commercial and residential properties — mastering financial planning, acquisitions, and growth strategy.
  12. Scaled a sustainable farming business from 20 to 1,000 hectares in under eight years — using his experience and scalable systems in a completely new field for him at the time.
  13. Secured multi million financing deals for property and agricultural development, balancing opportunity with long-term sustainability.
  14. Operated internationally for over a decade, leading cross-border teams across the U.S. and Europe with a deep understanding of global business dynamics.
  15. Leading through example, living the FreedomHub principles daily: integrity in action, commitment to growth, and synergy between family, people, and business.

Your new exciting milestones.

To get started on building more freedom into your life, download a free worksheet to start designing your best life/year.

Why Work with Madis

He’s walked the path.

Sales, leadership, entrepreneurship, investing. This is lived experience, not theory.

He keeps it simple.

No jargon. Just clear steps, numbers, and structures that you can use immediately.

He moves you into action.

Conversations lead to decisions; decisions lead to execution.

Clients often say the biggest shift is in how they think and decide — and that’s what changes their money, their business, and their leadership long term.

Next Step

If you see yourself in one of these:

you’re ready to grow your assets and build financial freedom,

you want to turn a business idea into something real and profitable, or

you need to get better results through people, not just your own effort –

then Madis is a strong partner.

Book a strategy call with Madis to:

  1. Map your current situation
  2. Clarify your long-term goal
  3. Decide what is your next best step

No fluff. Just a clear conversation and a concrete way forward.

contact me

Learn how we helped 100 top brands gain success