Chosen Theme: Investment Strategies for Entrepreneurs
The Entrepreneurial Investor Mindset
Entrepreneurs understand that not all risks are equal. Favor investments where downside is limited but upside can materially move your life. Small, repeated asymmetric bets preserve optionality while avoiding catastrophic, company-threatening losses.
Designing a Portfolio Around a Founder’s Life
Use a low-maintenance core that compounds quietly, like broad, low-cost indexes, then add satellite positions where you genuinely possess an edge. Keep satellites small and thesis-driven, with clear exit rules and review dates.
Where Entrepreneurs Have an Edge
Back problems you’ve personally endured, not abstract trends. Write memos, cap check sizes, and demand update cadence. Share your operating playbooks so founders benefit beyond capital. Comment with your memo template and we’ll share ours.
Where Entrepreneurs Have an Edge
Micro-acquisitions can yield steady cash flow and strategic synergies. Target boring, resilient niches with fragmented competition. Insist on clean books, customer concentration limits, and an integration plan before the letter of intent becomes binding.
Tax and Legal Efficiency for the Founder-Investor
Work with professionals to pick entities and accounts that match your strategy and jurisdiction. Separate operating risk from investment assets, and document intercompany transfers. A few setup hours can save years of compounding drag.
Even aggressive builders benefit from tax-advantaged accounts. Automate contributions, avoid frequent trading, and let compounding do the heavy lifting. Share your allocation mix and we will feature thoughtful examples in future breakdowns.
Loss harvesting is a risk tool, not a license for bad trades. Match gains and losses thoughtfully, maintain economic exposure, and record basis meticulously. Schedule a yearly review so decisions are proactive, not panicked.
Systems, Habits, and Decision Quality
Write a one-page memo before every position. Capture thesis, edge, risks, position size, and exit triggers. Revisit quarterly to learn from reality. Comment if you want our template and we will send a simple version.
Systems, Habits, and Decision Quality
On the calendar, every quarter: rebalance ranges, thesis updates, and red-team critiques. Pre-commit to actions before emotions spike. Invite a trusted operator to challenge your thinking and prevent comfortable, unexamined assumptions.
Systems, Habits, and Decision Quality
Define portfolio drawdown limits, single-position caps, and liquidity floors. If breached, execute predefined steps automatically. Guardrails reduce regret and keep the operating company insulated from investment turbulence and unexpected market shocks.
Real Stories from the Founder-Investor Path
The Illiquid Bet That Nearly Sank a Launch
A founder tied up savings in a long lockup private deal. When a supplier demanded prepayment, there was no cash. A simple treasury ladder would have preserved the opportunity and avoided stressful, value-destroying dilution.
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