Win Big by Starting Small
Lessons from The Art of War
When Big Bets Go Wrong
Years ago, when I was running a home health agency, I made what I thought was a game-changing decision. I invested more than $250,000 in a Honeywell® telehealth solution. I was convinced it would revolutionize patient care and drive growth for the agency. After all, I’d heard stories about agencies in Florida experiencing explosive growth with similar systems. I thought I was positioning my business for the next big step.
What I didn’t realize was that while the salespeople were great at selling the solution, the company wasn’t nearly as skilled at implementing it. After investing a ton of money, we were left scrambling to make it work. While we managed to use the system for a handful of patients, the results didn’t come close to justifying the cost.
Looking back, we probably could have tested the concept with a smaller, cobbled-together system for $10,000 instead of committing to such a huge investment upfront. Instead, I ended up learning a $250,000 lesson about the importance of starting small.
This morning, while reading The Art of War, I came across a passage:
“Take advantage of spots where he is unprepared, make repeated sorties…. Now if you reject this victorious strategy and decide instead to risk all on one battle, it will be too late for regrets.”
For small businesses, success rarely comes from betting everything on one idea. Instead, it’s about testing, adapting, and focusing on opportunities where others aren’t prepared.
Why Small Tests Lead to Big Wins
Sun Tzu’s strategy of “repeated sorties” is a reminder about the value of small-scale experimentation. Testing ideas in manageable ways allows businesses to:
- Minimize Risk: Avoid overcommitting resources to an unproven idea.
- Gather Insights: Use small tests to collect valuable data and guide future decisions.
- Adapt Quickly: If something doesn’t work, you can pivot without suffering significant losses.
Example: Imagine you own a bakery in a small town (the kind straight out of a Hallmark Christmas movie). Instead of overhauling your entire menu to focus on gluten-free and vegan options, you could start by adding a couple of gluten-free or vegan treats to your lineup. This way, you can see what your customers actually buy before making a bigger commitment.
(Side note: People often say what they think you want to hear, not because they want to lie but because they want to support you. Instead of just asking, let them “vote” with their dollars—you’ll learn what they really want. For a great book on this concept, check out The Mom Test.)
Finding Opportunities Where Competitors Are Unprepared
“Take advantage of spots where he is unprepared” encourages small businesses to find and focus on gaps in the market. These are areas where competitors are either unable or unwilling to compete effectively.
- Identify Weaknesses: Look for areas where your competitors underperform or ignore customer needs.
- Serve Underserved Markets: Focus on customers or needs that larger competitors might overlook.
Example: If you notice that other bakeries in town don’t offer treats for allergy-sensitive customers, your bakery could introduce gluten-free or nut-free options. This allows you to attract a loyal customer base without competing directly on price or scale.
(To learn more about identifying gaps in your competitors’ strategies, see this article from yesterday.)
Iterate Your Way to Success
The advice to “make repeated sorties” emphasizes the importance of agility and iteration. Instead of betting everything on one big idea, successful businesses test, learn, and adapt.
- Test and Learn: Start small, analyze results, and refine based on customer feedback.
- Stay Flexible: Be ready to pivot as market conditions or customer needs evolve.
- Build Incrementally: Use small successes to create momentum for larger initiatives.
Example: Your bakery could experiment with a limited-time seasonal offering, like peppermint bark scones. If they sell out, you know you’ve got a hit to add to your menu. If not, you’ve lost very little and gained valuable insight for the future.
Diversify Your Efforts to Minimize Risk
Betting everything on a single idea is risky. Diversifying your efforts allows you to:
- Protect Against Failure: If one idea doesn’t work, another might.
- Maximize Learning: Testing multiple ideas broadens your understanding of customer preferences.
- Increase Flexibility: A diversified approach makes it easier to pivot when necessary.
Example: Your bakery could test several customer acquisition strategies simultaneously: social media ads targeting local families, partnerships with nearby coffee shops, and in-store promotions for first-time buyers. Analyzing what works best lets you focus your resources where they’ll have the greatest impact while scaling back or iterating on the things that aren’t working.
The Danger of Betting It All
Ignoring Sun Tzu’s advice can lead to costly mistakes.
Example: Imagine you decide to roll out an entirely new product line—fancy custom wedding cakes—without testing whether there’s enough demand in your market. You invest in expensive equipment, hire specialized staff, and dedicate significant time to marketing. But after months of effort, you’ve only received a handful of orders, leaving you with mounting costs and no clear way to recover.
By starting small—like showcasing a few sample wedding cakes at local events or offering them as a limited-time option—you could gauge interest and refine your approach before committing fully.
Practical Ways to Apply This Strategy
If you want to avoid big bets and focus on thoughtful experimentation, here are a few steps you can take today:
- Identify a Small Experiment
Find one area where you can test an idea without overcommitting resources.
Example: Launch a limited batch of a new holiday treat, like cranberry-orange muffins, and see how customers respond. - Focus on Underserved Markets
Look for gaps in your competitors’ offerings and consider how you can fill them.
Example: Introduce nut-free cookie options to cater to families with allergies. - Diversify Your Initiatives
Try multiple small-scale strategies and compare the results.
Example: Run both an Instagram ad campaign and a local partnership with a coffee shop to see which drives more traffic to your bakery. - Reflect and Adjust
After testing, evaluate what worked and what didn’t. Use what you’ve learned to inform your next steps.
Example: If a seasonal product sells out, consider making it a permanent menu item or reintroducing it annually.
Big Wins Come from Small Steps
Sun Tzu’s wisdom is clear: betting everything on one idea is a dangerous game. Success in small business comes from testing, learning, and adapting. It’s about finding opportunities where others aren’t prepared and moving quickly but thoughtfully to seize them.
This week, take a moment to think about where you might be betting too much—or where you’ve hesitated to act because the risk felt too great. Identify one small step you can take to test an idea, fill a gap, or explore a new opportunity.
The path to sustainable growth isn’t paved with big gambles—it’s built on small, smart steps that lead to long-term success.
