How to Pivot Strategically in Business

If you’re leading a legacy business in transition, here’s one thing to remember: Transformations don’t happen all at once. They happen in steps. A recurring theme I see in companies trying to pivot: leaders swing too hard toward either aspiration or urgency but rarely balance both…. or they can’t push themselves out of their comfort zone and end up never swinging at all. The most successful growth strategies? They start where you are and build to where you want to go. That means crafting a multi-step transformation: Step 1: Generate momentum and capital. Identify high-confidence, low-risk growth opportunities that leverage what you already do well. These early wins fund the future and build belief. Step 2: Reposition the business. Lay down the scaffolding for the company you’re becoming, new business models, new capabilities, new customer value. Step 3: Transform. Make bold, foundational bets that open up your total addressable market, create defensible moats, and reposition your relevance for the next decade. But here’s the tough part: Transformation is as much about what you stop doing as what you start. Many companies fail at transforming because they simply just add more to their business vs focusing investments and execution. Focus is your friend! Great leaders don’t just set vision. They create sequencing, resourcing, and culture that makes change possible. Your first move doesn’t have to be your final one. But it has to be intentional, confidence-building, and value-creating or you’ll never get to phase two. If you’re a transformation leader, I’d love to hear how you’re approaching sequencing change and lessons learned. #Leadership #BusinessTransformation

You need to be able to pivot when business changes. In 2023, the drayage market changed drastically, and we found ourselves with lower rates and lower volume. I realized that I needed to look at new opportunities and new ideas. Until then, we’d only served customers within 150 miles from the port. But when I looked, I saw the need for longer-haul drayage. I shuffled things and we started serving customers up to 600 miles from ports. We took on customers in Buffalo NY, Columbus, OH and even all the way to NC. I think every business needs to expect the downturn and plan to be the one that will not only survive but thrive! Become the one who saw the needs before and the one who is the mainstay when others can’t pivot fast enough.    What are you doing to stay in the game no matter what comes at us?

I recently wrote a memo to the Iconic Arts team titled, The Art of Timing. I won't share the whole thing (it’s several pages long / intended for partners). But I thought it might be helpful to share some spark-notes for my entrepreneur and investor friends here on LinkedIn. As founders, we often focus on the 'what' and 'how' of our ventures, but the 'when' is just as pivotal. One of the biggest lessons I’ve learned after 10+ years in startup-ville with many failures and a couple exits, is that mastering the art of timing can be the difference between success and missed opportunities. Here are some key factors for us:  𝐔𝐧𝐝𝐞𝐫𝐬𝐭𝐚𝐧𝐝𝐢𝐧𝐠 𝐌𝐚𝐫𝐤𝐞𝐭 𝐑𝐞𝐚𝐝𝐢𝐧𝐞𝐬𝐬: Every groundbreaking company, product, or service has its time. Launch too early, and the market might not be ready. Launch too late, and we might be lost in a sea of competitors. We need to have our finger on the pulse, understanding when our audience is primed for what we're offering. 𝐒𝐩𝐞𝐞𝐝 & 𝐑𝐞𝐬𝐨𝐮𝐫𝐜𝐞 𝐀𝐥𝐥𝐨𝐜𝐚𝐭𝐢𝐨𝐧: Capital, talent, and other resources are finite. We must time our investments wisely, ensuring we're not spreading ourselves too thin or missing out on pivotal moments to accelerate growth. Speed reduces the idle time of resources and acceleration ensures that we’re maximizing the resources efficiently. a16z Games' Speedrun program really embraces this concept which is one of the reasons why we love them. Shout out to Joshua Lu, Robin Guo - great Spaces AMA yesterday btw. 𝐄𝐦𝐛𝐫𝐚𝐜𝐢𝐧𝐠 𝐭𝐡𝐞 𝐏𝐢𝐯𝐨𝐭: Just as timing is crucial in starting an endeavor, it’s equally crucial in recognizing when to pivot. Market dynamics shift. If we observe that our current path is not yielding the anticipated results, the timing of a course change becomes a strategic move. 𝐒𝐲𝐧𝐜𝐢𝐧𝐠 𝐰𝐢𝐭𝐡 𝐄𝐱𝐭𝐞𝐫𝐧𝐚𝐥 𝐅𝐚𝐜𝐭𝐨𝐫𝐬: Factors outside our control, like economic shifts, technological advancements, and even socio-political events, play a huge role in our venture's success. By staying informed and agile, we can align our strategies to capitalize on these external timings. 𝐏𝐞𝐫𝐬𝐨𝐧𝐚𝐥 𝐓𝐢𝐦𝐢𝐧𝐠: As leaders, our personal energy and focus ebb and flow. Recognizing when we're at our best (and when we're not) can be the difference between making a well-informed decision and a hasty one. 𝐅𝐞𝐞𝐝𝐛𝐚𝐜𝐤 𝐚𝐧𝐝 𝐈𝐭𝐞𝐫𝐚𝐭𝐢𝐨𝐧: Timing is also about rhythm. It's about introducing something, gathering feedback, iterating, and then reintroducing it. This rhythm allows us to continually refine and improve, ensuring that our offerings remain relevant and impactful. 𝐓𝐞𝐚𝐦 𝐒𝐲𝐧𝐞𝐫𝐠𝐲: This is a big one for me, maybe the most important. Just as with personal timing, ensuring our teams are synchronized and collaborating efficiently is essential. This ensures that our collective energy drives towards milestones at the optimal time. Matthew Medney, Jack Sheehan, Mo Yazdani, Kelly Duroncelet, Alec Roth, Aric Jain