The Shackleton Pact

When Ernest Shackleton recruited for his Antarctic expedition, he didn’t promise health care or a ping-pong table. He ran this ad:

“Men wanted for hazardous journey. Low wages, bitter cold, long hours of complete darkness. Constant danger. Safe return doubtful. Honour and recognition in case of success.”

He got thousands of applications. The 28 men who went with him all survived, and they achieved immortality.

Now consider the HMS Wager. Her crew was staffed by conscripts and men chasing a pension. When the same pressure hit, they didn’t rally. They mutinied, abandoned their captain, and descended into anarchy.

This is why the choice between venture capital and the Shackleton Pact is not only about cap tables or exits. It is the seed of your company culture.

Money acts as a genetic code:

• Salaries attract people who ask, “Is my job safe?”
• Equity attracts people who ask, “How do we win?”

You cannot rewrite this DNA later. If you fill the ship with mercenaries today, you cannot expect them to become missionaries when the storm hits.

In this document I will argue that the Shackleton Pact acts as a filter for soul. It has financial benefits, yes. But I find the cultural aspect even more enticing. It is not important to me that you take this route. What is important is that we explore the tradeoffs.

The Shackleton Pact

The concept is radical, but not new. At the end of the day, the only differentiator between this and a team of four buddies in their college dorm is that we can raise venture capital to pay salaries, but we are choosing not to.

Let’s start with what we would give an investor at this stage:

Instead of giving that equity to financiers, the Shackleton Pact gives the full 30% directly to the builders taking on some early risk.

It will not be easy. The obvious challenges are:

• Finding talent willing to work for no pay
• Keeping the cap table clean so future investment isn’t blocked if needed

There is another challenge of course around growth rates. Bootstraps often see 20-23% growth per year while venture-backed startups see 25-35% (per SaaS Capital ). That said, bootstrapped companies are 3x more likely to be profitable in year one.

In every decision you make, you should aim to reduce risk and hardship. Startups are risky enough as it is. But in this case the benefits of building a team of owners and forcing the discipline of bootstrapping are powerful. If you manage to survive, frontloading that pain will build a healthier, more resilient company.

Honor and Recognition

Shackleton promised honor if they succeeded. We are promising asymmetric upside.

The data shows that only 1% of seed-funded startups reach unicorn status. However, 20-30% of companies manage a successful M&A exit. The VC model requires the unicorn outcome to pay off. The Shackleton Pact wins on the base hit.

† Note: this depends on multiple factors (such as QSBS eligibility) and needs more research.

If we weigh these outcomes by their probability, the math shows a better outcome for builders:

• On the VC Path, team members take zero salary risk. Their EV is $26k over 7-10 years.
• On the Shackleton Path, team members risk ~9 months of no (or heavily reduced) salary. Their EV is $900k over a shorter time period.

We are asking talented people to trade short-term safety for a ~35x higher Expected Value.

The Invisible Army

I can hear it already: “That sounds great, but who can actually afford to work for equity?”

My confidence in this being viable comes from both intuition and data. Perhaps it’s the circles I run in, but I don’t see a shortage of developers just waiting for the right project to come around.

But when you add in the emergence of AI and general macro trends, I sense a perfect storm brewing and think we will see more bootstrapped companies emerge.

Here is the data on why they are available and why they fit the Shackleton Pact.

The Severance Class

In 2025, the tech sector saw massive job cuts.

• These were not performance-based fires. Many were strategic “delayering” cuts targeting senior leadership and high-cost architects.
• The average senior package included 20-26 weeks of pay. Combined with RSU acceleration , this created a class of workers with 6-12 months of personal liquidity.
• Many are not looking for another W-2 immediately. They are using this runway to de-risk their transition into ownership.

AI-Amplified Engineers

December 2025 and the release of Opus 4.5 marked a turning point. For top-tier engineers, the cost of writing code dropped to near zero, but the cost of deploying it inside a large company remained high.

• This is the senior engineer who uses AI to finish their assigned work on Tuesday, but has to wait until next Monday for the rest of the team to catch up. They are high-performance engines stuck in low-gear organizations.
• The Shackleton Pact appeals to them not because it’s “easy money” (it isn’t), but because it is an environment where they are allowed to run at full speed.

The venture market is currently overpaying for potential (25-year-olds) while undervaluing proven efficiency (35-year-old architects).

The Shackleton Pact exploits this inefficiency. You can recruit the seniors who have the financial runway to take a risk, and the technical leverage to build massive systems with small teams. They are out there, but they aren’t looking for jobs. They are looking for a place where their output actually matters.

The War Chest

Sweat equity cannot pay for servers. You would want to raise a tactical ~$250k war chest to cover the hard costs of the early days (infrastructure, legal, API credits).

You could raise this round on a SAFE with a valuation cap. Through the Shackleton Pact, you will have secured seven figures a year in talent effectively pre-paid via equity. The investors would be investing in a machine that is already built, fully staffed, and running at a fraction of the cost of a venture-backed competitor.

The Power of the Anomaly

Capital also carries the hidden cost of classification.

Right now, you are a myth: “the outsider who shipped a stable product without the usual résumé.” The market doesn’t know how to categorize you, which makes you dangerous. But the moment you take $5M from Sequoia, that mystique becomes a statistic: “The Venture-Backed Founder.”

We know that guy. We know his burn rate, his playbook, and his panic points. We can put him in a box, label him, and dismiss him.

But you can refuse the box.

Remain the anomaly. Use your experience and the work you’ve already done to inspire a world-class team to follow you on a hazardous journey.

The Privilege of Leading Men

Regardless of whether you take VC money or not, you are inviting your team into a dangerous, high-stakes pact. The unspoken contract with every person you bring onboard is simple but carries weight:

“Following the founder will bring me financial success.”

They will talk about you at their dinner tables. Their spouses will ask if “this startup thing” is worth the risk. You are responsible for the answers to those questions. If the company’s value goes to zero, you will have wasted years of their lives.

The Shackleton Pact leans into this responsibility.

It is a declaration from day one that you care more about the builders in the boat than the bankers on the shore. It offers your team the agency and ownership they crave. But we do not give this power away; it must be earned. To gain the upside of an owner, they must sacrifice the safety of an employee.