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47 litigations. That’s how deep the hole got after Geetanjali “Gee” AlamShah’s airline bet went sideways and it’s also the most hopeful part of this conversation: she climbed out. Not by pretending it didn’t hurt, but by getting disciplined, getting help, staying intentional, and refusing to lose hope.

Gee is a first-generation entrepreneur who scaled a travel business, then made a bold, high-risk jump into aviation launching an international India route (Delhi–Baku–Delhi) by wet-leasing an aircraft from Azerbaijan Airlines. She didn’t raise capital; she leveraged herself and moved fast, even securing a license that others didn’t think she could get.

But aviation is a brutal business: fixed costs don’t care about your confidence, and every empty seat burns cash. She ran out of money in late 2019 and paused, planning to relaunch in March 2020. Then COVID hit. That unexpected global pause, oddly, became her one blessing: it gave her time to put her house in order.

The shutdown phase was ugly: 47 litigations, near-bankruptcy stress, and the emotional weight of facing employees, peers, and the world. What helped was community and clarity, especially the Harvard OPM network that pointed her to the right people and advice. The best guidance she received was simple and humane: put your own oxygen mask on first, but never forget the intention to pay people back over time.

From that rubble, she rebuilt launching two new businesses in 2022:

• Voyage of Wellness
• Ed2Careers

Her reset wasn’t just strategic; it was personal. She leans hard on fitness, meditation (Vipassana), structure, and intellectual. She wakes early, meditates, trains/runs, journals at night, and spends serious time networking and learning. Her kids now run key parts of the businesses, she provides vision, strategy, and business development.

And here’s the thesis she repeats like a mantra: hope isn’t a plan… until everything else is gone. Then hope becomes the only plan. Jim Collins told her: don’t lose hope, don’t lose faith in who you are. Because you’re only smarter now.

Here are the Top 10 Takeaways from the conversation:

1. Failure does not define your worth; it only reveals what didn’t work.
2. Confidence often peaks right before real learning begins.
3. You must survive first before you can fix everything else.
4. Clear intention and honesty matter more than flawless outcomes.
5. Structure and routine keep you steady when motivation disappears.
6. Community helps you think clearly when isolation distorts reality.
7. Starting again is never starting from zero when you’ve lived the lessons.
8. You don’t need certainty to move forward - only the willingness to take the next step.
9. Holding on to the past can quietly block future progress.
10. When all strategies fail, hope becomes a conscious, daily choice.

Books:

• Autobiography of a Yogi
• Good to Great
• How the Mighty Fall

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Imagine waking up every day knowing your job is to suffer on purpose because that’s the price of building something that can dominate a category. Brad Cowdrey (OPM 49) explains why startups aren’t glamorous, why GenAI changes what “coding” even means, and how his company eveoy aims to let brands “fill stores with people” on demand.

Brad describes himself as a deeply hands-on angel/operator often acting as CEO, CTO, and sales driver because he likes control, speed, and talent development. His core philosophy: don’t just write code; build systems that write code, a mindset he learned early while working around supercomputing. Today, he’s pushing engineers to shift from “coding” to higher-level thinking: prompting, agent swarms, and automation patterns that amplify output in the GenAI era.

He traces his start to Colorado Springs’ military-tech ecosystem, where, as a teenager, he got unusual access to hardware, operating systems, repairs, and low-level computing forming a fearless “just learn it” habit: call experts, ask questions, and build anyway. That foundation led to a lifelong obsession with data: he sees data as the exhaust of human behavior and prefers scientific decision-making over intuition dressed up as analytics.

He also shares a leadership model: startups move through distinct phases of construction, prototyping, operations and the CEO must change tools, tone, and org design accordingly. His daily resilience practice is simple but rigorous: reconnect to life goals every morning, pick 1–2 must-win actions for that day, and compound progress. OPM’s lasting value for him is the people, global perspectives, long-term friendships, and even meeting his co-founder.

Here are the Top 10 Takeaways from the conversation:

1. Startups are “pain and suffering” by default—don’t enter if you’re optimizing for comfort.
2. The new edge is “code that writes code.” GenAI pushes developers upward: design systems, workflows, and prompts/agents—not just features.
3. Invest in people, not just products. Brad gets energy from stretching teams from doers into independent thinkers.
4. Fear is usually fake data. His life pattern: stare it down, call someone, learn fast, build anyway.
5. Data = exhaust of human behavior. Use it to decide, not to justify decisions you already made.
6. Go for problems big enough to matter. He’s now only excited by “game-changer / category-creating” plays.
7. Category creation is brutal. If there’s no competitor to copy, expect repeated build-destroy cycles until fit emerges.
8. Sustainable businesses create clear value for every stakeholder. If one side of the system feels like it’s “doing work” while the other extracts value, the model eventually breaks.
9. Know what phase you’re in. Construction vs operations require different leadership styles; mixing them breaks momentum.
10. Resilience is daily re-anchoring. Re-state your life goals each morning, pick 1–2 critical actions, and let compounding do the rest.

Books: Good to Great

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K. Sudarshan is a veteran executive search leader and Managing Partner at EMA Partners across India, Singapore, and the UAE. Sudarshan shares his journey from an accidental recruiter to building and listing one of India’s largest executive search firms. Drawing from 25+ years of experience working with founders, boards, and CEOs, he offers deep insights into leadership, talent decisions, governance, and scaling professional services firms.

The conversation explores why executive search remains critical despite democratized talent data, how boards underestimate CEO onboarding, and what founders and organizations must unlearn when hiring senior leaders. Sudarshan also reflects on entrepreneurship, long-term value creation, people-centric leadership, the impact of fitness and endurance sports on mindset, angel investing, and lessons from Harvard Business School’s OPM program. Throughout, he emphasizes perspective, trust, frugality paired with ambition, and building institutions that outlast founders.

Here are the Top 10 Takeaways from the conversation:

1. Entrepreneurial roots matter
   Growing up in a business family shapes risk appetite, frugality, and long-term thinking even when careers start accidentally.
2. Think small, think big
   Run operations frugally (“think small”) while holding bold, long-term vision (“think big”).
3. Best candidate ≠ right candidate
   Executive search is about contextual and cultural fit, not just credentials or network-driven hiring.
4. Executive search blends art and science
   Assessing leadership fit requires structured evaluation and human judgment.
5. Every company and founder is vulnerable
   Talent, continuity, and uncertainty affect startups and billion-dollar firms alike.
6. People outperform ownership in professional services
   Overplaying professionalism and performance builds stronger, longer-lasting firms than equity-focused models.
7. CEO onboarding is widely underestimated
   Integration and cultural assimilation matter as much as selecting the right leader.
8. India’s leadership landscape has shifted
   Professional CEOs now dominate over promoters, reflecting stronger governance and global scale.
9. Perspective anchors leadership in tough times
   Avoid knee-jerk decisions, trust proven performers, and remember that downturns are temporary.
10. Long-term success is about credibility, not money
    Respect from clients, repeat relationships, and trust define sustainable success more than short-term financial metrics.

Books:

• Straight from the Gut
• Execution
• No Rules Rules

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Alejandro Diez Barroso explains how bootstrapping two early e-commerce businesses in Mexico taught him the real constraint in many markets: access to growth capital. He sold not because he wanted to, but because scaling required funding and institutional readiness. That experience shaped DILA’s mission of investing across the Spanish-speaking world and helping founders build venture-backable companies with clear liquidity paths.

He breaks down how exits actually happen , why governance/financial hygiene determines deal certainty, and why many founders misunderstand term sheets, especially preferred shares, liquidation preferences, and drag/tag rights. He also shares how LatAm is evolving from “copycats” to “tropicalized” models and increasingly global products, while still needing more liquidity events. Personal themes: know your business type (sell vs lifestyle), match capital to incentives/time horizons, make customers “heroes” (even when you have two), practice patience/compounding, and master selling as a foundational founder skill.

Here are the Top 10 Takeaways from the conversation:

1. Build type matters: “Built to sell” and “lifestyle” businesses require totally different strategies and only some are venture-fit.
2. Capital is a commodity; alignment isn’t: Choose investors by incentives, timeframes, and behavior in bad times—not just valuation.
3. Don’t raise money “because”: VC brings an implied exit clock and shared control; many founders accept this too late.
4. Liquidity is hard, so be prepared early: Deals fail less from price and more from messy governance, weak reporting, and diligence surprises.
5. Valuation is only one term: Preferences can make a “big exit” pay founders little or nothing if the pref stack is heavy.
6. Avoid toxic structures: Participating preferred (and high multiple prefs) can be brutally expensive for founders.
7. Board/control discipline: Don’t lose board control too early; it can force decisions (including sales) you didn’t intend.
8. Drag/tag rights are not fine print: They can compel a sale or force you to buy out investors at offer terms—know what you’re signing.
9. Selling timing is often opportunistic: Great companies attract unsolicited offers; the “right” time is when risk-adjusted certainty is compelling.
10. Founders who compound can sell: Selling isn’t just customers. It’s vision to hires, cofounders, investors, partners, and the market.

Books: The Hard Thing About Hard Things

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If your business outlives you, have you clearly written what you want it to mean and how decisions should be made when you’re no longer there to make them?

For business owners, Trusts are powerful tools, but their effectiveness often hinges on one document that gets far less attention: the Letter of Wishes.

Juan Carlos Almanza emphasizes that many successful entrepreneurs approach Trusts as a one-time legal task, rather than a living framework for legacy, governance, and family alignment. Trusts can protect assets, transfer wealth, and preserve control across generations—but documents alone don’t capture intent, judgment, or values.

That’s where the Letter of Wishes comes in. A Letter of Wishes is a non-binding written document created by the founder to guide trustees and family members. It explains why the Trust was created, how decisions should be interpreted, who is best suited for leadership or control, and what values should guide distributions and governance. Unlike legal agreements, it allows the founder to speak in human terms (context, philosophy, and nuance) so future decision-makers understand not just what to do, but why.

Without a clear Letter of Wishes, even well-structured Trusts can fail in practice. Ambiguity around fairness, control, or responsibility often leads to conflict, misaligned incentives, or erosion of the founder’s original vision. With it, Trusts become adaptable, values-driven systems rather than rigid legal shells.

Here are the Top 10 Takeaways from the conversation:

1. Trusts are operating systems, not paperwork. They require intent, governance, and active use.
2. Earlier planning strengthens Trusts. It shows purpose beyond tax and allows evolution over time.
3. Trusts don’t work on autopilot. Actions must align with written rules.
4. Purpose comes before structure. Define fulfillment before dividing assets.
5. The Letter of Wishes is the voice behind the Trust. It translates legal form into practical guidance.
6. Clarity beats equality. Fairness may mean different roles, not equal outcomes.
7. Writing reveals truth. Founders often don’t know what they want until they articulate it.
8. Business reality first, tax strategy second. Optimize only after aligning incentives and goals.
9. Strong estates are layered. Trusts, holding companies, and operating entities each serve distinct roles.
10. Customization is essential. Effective Trusts reflect real families, not templates.

Books:

• Catcher in the Rye
• As a Man Thinketh
• Think and Grow Rich
• Modern Man in Search of a Soul

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This conversation is less about legal theory and more about the emotional weight of being a lawyer. Through Felipe Barreto Veiga’s story, we see a profession defined by responsibility, sacrifice, and quiet loyalty. Being a lawyer, in his telling, means carrying the client’s anxiety as your own, standing beside them in moments of uncertainty, and showing up fully even when it costs personal time, comfort, or balance. It’s a reminder that law is not just a career—it’s a demanding commitment to always be prepared, emotionally present, and relentlessly aligned with the client’s best interests.

Felipe Barreto Veiga—founding and managing partner of BVA Law Firm in Brazil—shares his journey from modest early jobs to building one of the country’s most respected corporate law firms.

Felipe reflects on leadership lessons from advising entrepreneurs and investors, emphasizing the importance of “seeking the truth” in markets often distorted by hype, inflated valuations, and short-term thinking. For him, good lawyers and good leaders must be honest with clients, even when the truth is uncomfortable.

A central theme throughout the conversation is loyalty. Felipe describes the lawyer as a “loyal squire” - someone who stands beside the client in both moments of victory and crisis.

Felipe is candid about work-life balance, arguing that it does not truly exist in law. Instead, lawyers experience cycles of “war and peace,” where intense demands from clients can override holidays, family plans, and personal time.

He also addresses the structural challenges faced by women lawyers and working parents, acknowledging the uneven burdens while stressing flexibility, empathy, and institutional support as essential for retaining talent. His reflections on upbringing, curiosity, resilience, and relationship-building reinforce the idea that successful lawyers combine technical excellence with emotional intelligence and human connection. Ultimately, Felipe returns to a single truth: law, business, and leadership are all about people.

Here are the Top 10 Takeaways from the conversation:

1. Being a lawyer is an emotional responsibility
   Lawyers don’t just manage transactions—they absorb client stress, uncertainty, and pressure.
2. Loyalty to the client comes above all else
   A lawyer’s role is to stand beside the client, even when advising against a deal.
3. There is no true work-life balance in law
   The profession operates in cycles of “war and peace,” driven by client needs.
4. Putting the client first requires real sacrifice
   Holidays, nights, and personal plans may be lost when the client is in crisis.
5. Protecting the client matters more than closing deals
   Success is measured by judgment and integrity, not transaction volume.
6. Truth is a critical leadership skill
   Great lawyers and founders cut through hype and face reality, even when it’s uncomfortable.
7. People—not deals—are the core of the business
   Talent, trust, empathy, and accountability determine long-term success.
8. Flexibility retains great lawyers, especially parents
   Understanding life outside work builds loyalty and sustainable performance.
9. Teaching and learning sharpen judgment
   Exposure to diverse perspectives makes lawyers better advisors and leaders.
10. Excellence is expected at all times
    Whether negotiating, advising restraint, or offering reassurance, lawyers must always bring their best.

Books: Good to Great, No Easy Day

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A single sentence from his mother "If you go to the US, you may never come back… and it may be too late” rerouted Pramod Maheshwari’s life. In that moment, ambition met responsibility. He stayed back in Kota, not with a grand plan, but with a quiet resolve to honor relationships and make his choice worth it. What followed is a story of turning uncertainty into purpose and a relentless commitment to excellence that eventually helped build Career Point into a multi-vertical education institution serving tens of thousands of learners each year.

Pramod Maheshwari shares how he moved from being an unemployed IIT Delhi graduate in 1993 to building a large education enterprise spanning test prep, schools, and universities. His early breakthrough came from teaching physics to a small group of IIT-JEE aspirants; strong results created trust, momentum, and eventually Kota’s coaching ecosystem. He credits relationships as the most important “balance sheet,” echoing lessons from Harvard’s OPM.

He speaks openly about the doubt of choosing an unconventional path while peers thrived abroad. The dot-com era became a turning point - he chose to commit, not regret, and scaled Career Point. He frames IPOs as a mindset of shared responsibility, warns against excess capital, and anchors everything in one belief: pursue excellence, protect cash flows, and build systems that let ordinary people do extraordinary work.

Here are the Top 10 Takeaways from the conversation:

1. One emotional truth can outweigh a thousand career plans. His mother’s words reframed success as responsibility, not just achievement.
2. Your “relationship balance sheet” can be your strongest asset. He credits parents, brother, wife, and team as the foundation behind everything else.
3. Start small, but start real. A tyre godown + ₹25,000 + one ad + daily preparation became the seed of a movement.
4. Early results build belief—and belief compounds. First-year outcomes created credibility and a flywheel of trust.
5. Comparison can poison you—or propel you. He spent 7–10 years doubting himself versus US-based peers, then used that pressure as fuel.
6. Excellence is a strategy, not a slogan. His mantra—pursue excellence and everything else will follow—guided decisions across decades.
7. Scale quality with systems, not heroes. Standardized teaching delivery, assessment, feedback loops, and 3–6 months of faculty training made outcomes replicable.
8. IPO readiness starts with mindset: share wealth, share responsibility. Public capital brings accountability; your wealth depends on shareholder wealth creation.
9. Too much capital can lead to wrong decisions. Abundance tempts overreach so capital allocation discipline matters.
10. Don’t react—respond. OPM reinforced calm decision-making, respect for teams, and the idea that execution decides whether strategy succeeds.

Books:

• The Dhandho Investor
• The Art of Clear Thinking

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What if you could hear, firsthand, from an international sportsperson about the emotional journey that follows a loss?

Not loss as failure, but loss as a teacher: the kind that strips away ego, demands honesty, and forces you to confront your preparation, your mindset, and your emotional control. Hari Kiran has lived this cycle—on the badminton court, on global stages, and in the unforgiving world of regulated industries and entrepreneurship.

As an international sportsman, Hari (founder of HRV Pharma) learned early that losing is brutally transparent. There’s nowhere to hide, no committee to blame, no narrative to spin. The scoreboard tells the truth. And that truth forces introspection.

What stands out is how calmly Hari speaks about this journey. There’s no romanticizing intensity, no performative hustle. Instead, there’s a quiet respect for systems, discipline, and repeatability. He talks about learning to reset emotionally, about not letting one bad point become two losses, and about showing up again even when the outcome previously went against you.

The episode also gently reframes success. Early on, success was visible—rankings, scale, recognition. But after losing on big stages, success becomes quieter and more durable. It becomes about building systems that don’t depend on you, cultures where people can make decisions without fear, and organizations that can absorb mistakes without breaking. It’s about trust compounding over time, not applause in the moment.

Ultimately, this episode feels less like advice and more like an invitation: to slow down after losing, to stay emotionally steady, to close the feedback loop honestly, and to redefine success not by how fast you move—but by how long what you build can last.

Here are the Top 10 Takeaways from the conversation:

1. Losing teaches what winning never will
   Winning hides flaws. Losing forces honesty. The real failure isn’t the loss—it’s walking away without learning.
2. Emotional control is a competitive advantage
   Carrying the last mistake into the next point means losing twice. The ability to reset quickly matters more than intensity.
3. Discipline sustains what talent starts
   Talent opens doors, but discipline—training, recovery, repetition—determines how long you stay in the game.
4. Preparation doesn’t guarantee outcomes, but it earns you another attempt
   You can do everything right and still lose. That’s not a reason to stop—it’s a reason to prepare better and keep playing.
5. Judge decisions by process, not by outcomes
   In both sport and business, outcomes are noisy. Strong systems and thoughtful decision-making compound over time.
6. Capital can’t fix weak foundations
   Money won’t rescue you from poor capability, low credibility, or fragile relationships—it often accelerates collapse.
7. Trust is an invisible but powerful currency
   In high-stakes, regulated environments, trust shows up in speed, access, forgiveness, and long-term compounding.
8. Success matures from visibility to durability
   Early success is loud. Real success is quiet—systems that work without you, cultures that don’t fear mistakes, lives that still feel whole.
9. Trends begin as friction, not headlines
   Pay attention to inefficiencies, workarounds, and handoffs where systems strain—this is where meaningful change starts.
10. Build before you bet
    Capabilities, discipline, and trust come first. Without them, risk is gambling. With them, risk becomes progress.

Books: The Art of War