The 3rd Rail Entrepreneur: Recent Episodes
Alastair Macdonald
A podcast about enrichment. Enrichment of our minds, relationships, meaning and business via the entrepreneurial path. We'll share Alastair's real-time business case studies with private clients, stories from the field, legends and cross-pollinatory musings to inspire and provoke your own creativity. Join us! Facebook Group: https://www.facebook.com/groups/3rdrailentrepreneur
An employee asks for a raise. You feel defensive. They double down...so do you. It's all a misunderstanding rooted in a scarcity mindset that undermines true entrepreneurship.
Do what you do. Love what you love. But as the cycle changes, optics really matter. Here's how.
This single concept transformed everything for me. Embracing and embodying it has had a profound impact—and it has the power to radically change your life, too.
How and why we lower the bar for friends and family. How and why it’s a bad idea to do so. Looking back on a powerful lesson from my very first mentor.
How to navigate market and economic volatility with clarity and caution—where success is defined differently. Highlighting the hidden cost of current tariff policies, framing them as a “sword without a shield” that harms U.S. consumers more than foreign adversaries. It’s a timely call to rethink risk, resilience, and what real protection looks like.
We continue to unpack how the collapse of global cooperation—once maintained under Pax Americana—has given way to a multi-player world of economic self-preservation and escalating risk. Using game theory and historical precedent, I'll explain why recent U.S. tariff policies may trigger long-term consequences with no clear upside. This is a must-listen framework for understanding the new rules of global business and the mindset needed to adapt.
Don't skip this - We explore the end of Pax Americana and the beginning of a new global order shaped by tariffs, fractured alliances, and ideological calcification. This foundational conversation offers historical context, current implications, and future-facing strategies for navigating an uncertain global landscape.
My personal journey. Social, economic, financial destruction, resurrection and triumph. Charting a course through cycles.
Change is here. Some are blind to it. Some are ignoring it. A few will embrace it. I know what camp I'm in. You ... ?
Part 2 of The Partnership Paradox
- Partnerships done well and those done badly
- Where do they unravel and why?
- Contribution, reward and more
- Partnerships done well and those done badly
- Where do they unravel and why?
- Ownership rights vs. voting rights
- Contribution, reward and more
A historical context of today’s environment and the less discussed, other side of interest rates.
- 1720 all over again?
- Blank-check companies and secret promises
- Paying different attention to lower interest rates
'Stimulus packages are going to destroy the dollar and increase inflation.' Makes sense, but is that true?
The best business decisions are made by the best decision makers. How can we improve our understanding of group and cultural dynamics?
- The insights of game theory
- Geo-political shifts and America's move within
- A better understanding of macro-dynamics will better help with our micro-decisions
How do we identify the cycles that we're creating?
- Identifying the differences between the tax, economic and financial cycles
- Understanding inflation
- The role of chance, people and events in our lives
- Identifying those that change the course of our lives
- Honoring and being that change for others
We're upgrading and excited to announce a secret co-host. In this episode, Alastair and "secret co-host" discuss ambition, the entrepreneurial path, Counsels of Elders and more.
- What happens when one party chooses the risk and the other pays the price?
- Too big to fail, too expensive to bail.
- Is it really stimulus or merely support?
- The long-term cost of stifled innovation.
- What really moves an economy.
- What real help looks like.
- Creative destruction and moral hazard.
- The suffocation of entrepreneurship and ignoring the wisdom of our economic elders.
During a private training session, Alastair presents the concept of The Micro-Harvest. Early on in our entrepreneurial paths, we convince ourselves that “x” is freedom (money). We then fold it back on itself, because it hasn’t arrived, ultimately deferring joy in the process. The Micro-Harvest allows: freedom from, freedom to do, and freedom within.
Sometimes the areas that we grow in the least contain the stuff that we know the best. What to do about it.
With record unemployment levels in the US, the urge to support the less fortunate is clear and overwhelming. In doing so, we have to ask ourselves about the second-order consequences.
While lowered interest rates and access to unlimited credit from the Federal Reserve seem like a panacea, we need to be very wary of the long-term, downstream and multi-generational effects. Here’s how it works.
This episode is a short excerpt from a private-client-group training where Alastair discusses the Time Harness strategy.
In Part 2 of this special episode, revisit how society, finance and economics manifests in art, design, theater and politics with Anahit Hakobyan's (Viva La Flora podcast) interview with Alastair. Developing and understanding an awareness of these interwoven elements is a significant step in becoming a Full-Cycle Entrepreneur.
Check out Anahit's other episodes at Viva La Flora: https://podcasts.apple.com/us/podcast/viva-la-flora-live-the-art-and-business-of-flowers/id1472056410.
In this special episode, revisit how society, finance and economics manifests in art, design, theater and politics with Anahit Hakobyan's (Viva La Flora podcast) interview with Alastair. Developing and understanding an awareness of these interwoven elements is a significant step in becoming a Full-Cycle Entrepreneur.
Check out Anahit's other episodes at Viva La Flora: https://podcasts.apple.com/us/podcast/viva-la-flora-live-the-art-and-business-of-flowers/id1472056410.
In this episode, Alastair brings his first guest - Dr. Brady Marshall - onto the show. We work every day to give more, in order to gain more - fame, status and cash. But there are far more rewarding riches in your business that you are yet to know exist.
The medical, economic and social risks of COVID-19 are by now, obvious. What's not, is the most insidious risk of all.
Understanding the business cycle requires knowing how money flows through industries, banking systems and global financial-institutions. In order to understand where the money is going next, we need to know where the money came from. In this excerpt, from a live training for dentists, Alastair finishes 'How We Got to Now'.
While it may feel that the world has gone mad because of COVID-19, there’s a lot more at play. This is the background story of how we got to now.
This is another 'Touching the Rail' (TTR) episode, where we bring you disparate thoughts and ideas and little mementos to enrich your experience. We hope that you find a moment of enrichment within.
The first episode in the 'Touching the Rail' (TTR) installments, where Alastair shares words for you to ponder and make use of in your own lives. Right now, when we are all being forced to come up for air and take a pause from our regular, insane lives, it’s an opportunity to reflect on the instincts and propensities that we have – culturally and individually. Take this pause and find reflection in your life through Alexis de Tocqueville's words from Democracy in America.
The four components of the current social discontent. The best way to solve a problem is to break it into its component parts. In this episode, we cover what those pieces are that are affecting all of us – the economic, the medical, the social and the political.
The value of experienced advice. Identifying the biggest flaw in our natural, human instincts. Separating those who cheerlead, from those who add value. The comfort and power of intellectual courage.
The last several weeks have revealed so many things - our agreements, supply chains, assumptions, medical care, sense of commitment to each other, money, debt and the future.
7 trillion dollars erased in 3 1/2 weeks. Where did it go? Jeff Bezos worth 110 billion dollars. Really?
Every liquid market is an auction market. Is now a time to buy? Stocks are now cheap, but will they get cheaper? As entrepreneurs, what exactly is our job right now?
As entrepreneurs, understanding the nature of recessions and contractions will help inform us how we can best prepare ourselves and our profits, where possible.
The US markets and economy are approaching the tail end of their longest expansion in history. Half of a complete business cycle is behind us. What’s next?
Principles, philosophies, priorities, beliefs are all things that we’re sure are of our own design. But are they really? Or are you mimicking the beliefs of others?
The three critical skills to acquire and cultivate for a business and a lifetime of growth.
Ever notice how some people never seem to go without opportunities? Without clients, work, customers, patients or invitations? What is it about them? They can do something that few else can. It's here. In a short story, from 1899.
Your business can do so much more for you than providing money and status. It can and should create insights, education and creativity that carry over into all domains of your life.
How could we possibly find solutions to a problem that is misdiagnosed? In the conclusion to Episode 7: Diagnosis and Prescriptions: Part 1, Alastair talks about the three critical questions to get to the heart of the matter.
We're constantly misdiagnosing our problems and in so doing, we view the symptoms as problems. In this week's episode, Alastair takes his experiences with private clients and discusses that the biggest mistake an entrepreneur can make is mistaking symptoms for problems. He highlights why it happens and how you can fix it.
The perceived leader vs. the actual leader, a tale of the two. In this episode, Alastair reflects on his time spent on Wall Street and shares his observations of two of Wall Street's biggest business executives.
Alastair presents at a DSI Summit and discusses Dark Matter. We only know it by its opposite; we don't know the value of it and yet we're actively experiencing it. Alastair posits that only when we embrace it can we turn it into a superpower.
Every leader has a philosophy either inherited or created. In this episode, Alastair shares two critical first-principles.
The entrepreneurial path is a loop from ignorance to insight to wisdom, back to ignorance. Alastair shares a story from the inner circles of American power.
The new frontier of entrepreneurship and what lies beyond profit. Alastair discusses the adventures of business, as a vehicle towards growth - more than just money.