Whale Hunting and Fishing: A Survival Guide for Startups and Scaleups
In the wild seas of entrepreneurship, two strategies often define survival and success: whale hunting and fishing.
Whale hunting is the pursuit of massive clients — Fortune 500s, government contracts, or multinational partners. These are game-changing deals. One contract can transform a business. But whales are elusive. They move slowly. Procurement cycles stretch for months, sometimes years. Decision-makers change. Budgets shift. Legal redlines drag. And until that whale is harpooned, celebrated, and reeled in… you’re still adrift. Whales provide large cheques, logos for marketing and case studies…you will crush it when you land a whale.
Meanwhile, fishing — the act of consistently catching smaller, quicker clients — keeps the crew fed. It’s the bread and butter: small-to-mid-sized businesses, pilot programs, beta users, recurring subscriptions, individual consulting gigs. It doesn’t get the same headlines, but fishing provides cash flow, traction, feedback, and critical momentum. Trust me…you need to eat fish while you hunt whales! There are no big paydays, logos but what you get is cash…now (and trust me, you will need it)! You can also get some good case studies to help land a future whale.
Many founders make the mistake of betting everything on the whale (the author included). They stop fishing. They build for a client who hasn’t signed. They stretch their runway, drain resources, and lose optionality. When the whale swims away — or worse, ghosts you after 12 months of meetings — the boat sinks. (we had a $50M bid with a massive company that took over 4 months of hard work for our entire team, only to lose the bid and get $0.00 for our efforts despite the fact the management firm got paid their $1000/hour rate).
The real art is doing both.
The Case for Whale Hunting
Whales are worth chasing. A single enterprise deal can:
- Validate your product at the highest level.
- Provide 12–36 months of predictable revenue.
- Open doors to global networks, press, and follow-on funding.
- Get Fancy Logos to put on your website (like ours at METAVRSE.com)
But whale hunting is expensive and slow. You need the right introductions, legal prep, procurement readiness, enterprise security standards, compliance reports, and the patience of a monk. If you’re not careful, chasing a whale without a backup plan can become fatal.
The Power of Fishing
Fishing is scrappy. It’s fast, iterative, and builds confidence. Every “yes” builds morale and your bank balance. You get:
- Valuable feedback loops to refine your offering.
- Real-world case studies and testimonials.
- A growing community of users and champions.
- Revenue that doesn’t require navigating 14 procurement departments.
Fishing also creates a sustainable ecosystem. It funds your operations while you keep the harpoon sharpened for the next big shot.
The Dual Strategy
Smart founders master the art of hunting while fishing:
- Segment your team: Have sales development reps (SDRs) or account executives (AEs) who specialize in quick-win deals while others focus on enterprise. Offer quick hit bonuses for fish and big bonuses for whales….remember cash is still king.
- Design your product with modularity: Offer smaller packages or features for SMBs while building toward robust solutions for the enterprise.
- Use fishing to fuel hunting: The success stories from smaller clients become ammunition when you approach whales. Your traction becomes your credibility.
- Build brand and visibility: While whales may take months to move, they’re always watching. Be visible. Thought leadership, community events, press, and partnerships can all influence slow-moving giants.
Final Thoughts
Whale hunting is seductive — and rightly so. It can change everything. But unless your startup has deep capital reserves or is already profitable, chasing whales alone is a dangerous game. The founders who survive — and thrive — are those who know how to balance the dream of catching a whale with the discipline of fishing every single day.
Feed your team. Keep the lights on. Build traction. And when the time comes, be ready — harpoon in hand — to land the whale that changes your company forever.
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AlanSmithson.com — Founder, Father, Futurist, Author & DJ
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