Headwinds, Crosswinds and Tailwinds: Surviving and Thriving

Beth Cochran
Apr 6 · 4 min read

Authored by Tom Curzon, StartupAZ Foundation Chairman

Devastation and loss from the novel coronavirus pandemic seems to know no boundaries, and the startup world isn’t immune. While isolation and hunkering down is an appropriate strategy for personal safety, for some, particularly founders/CEOs, hunkering down as a business strategy may not lead to anywhere good. No doubt that while there are roughly a zillion different things a startup CEO could do, I have observed that at least one potentially helpful tactic is to take note of your headwinds, crosswinds and tailwinds, and respond accordingly.

So what do I mean? Pretty simple — think about the wind and its effects during any number of outdoor activities. Maybe you are running, golfing, sailing or biking, the wind impacts your performance one way or another. And while it might be changing around you, your performance depends on how you might change your own tactics once you recognize what is going on at the moment.

Here are some current lessons and wisdom from CEOs in our StartupAZ Collective:

From Christie Kerner, Fearless Leader, and now Founder/CEO of My Little Mascara Club:

  • It is important to recognize in the moment what the forces at play might be so you don’t make long-term decisions counting on what might be a tailwind effect that could change or giving too much weight to temporary data from a headwind.
  • She noted that when the pandemic first started, just as she was launching, the uncertainties of the moment with the lockdowns caused a headwind where her customers stopped shopping. Knowing this was temporary but still needing to meet them where they would spend, she found her target audience investing in playing games on their phones! By incenting them to try her product for points in their game she was able to get many new customers, until….
  • What seemed like a happy tailwind became an unproductive crosswind, or maybe even a headwind. When August and in-home schooling resumed, moms no longer had time for games. As they became Chief Teachers, conversions and revenue took a hit.
  • Now that her network of traffic sources has diversified there is less impact on revenue from a single-source headwind or tailwind. However, she still monitors things like the temporary headwind of rising paid social costs during this unusual Q4 and both measures her growth investments + the monitors the data with this context in mind.
  • Christie feels that the key value in noting a headwind, tailwind or cross-wind is to be aware that it exists so you can shift your read of the data and make decisions accordingly.

From Russ Perry, Founder/CEO of Design Pickle:

  • Design Pickle is a subscription workforce solution, initially targeting marketing/creative services.
  • What initially seemed like a headwind as the shock of the initial lockdowns created marketing uncertainty, DP quickly found that tailwind conditions they could take advantage of:
  • The supply of creatives looking for part-time gig work in the creative space suddenly and dramatically increased AND
  • As DP’s target market of SMBs began downsizing under cash pressures and released marketing employees, they realized they still had creative needs and Russ believes that the circumstances made a lot of companies much more willing to embrace a fractional solution like DP’s.
  • Where Russ does believe he’s seeing at least crosswinds if not headwinds is in the capital market, as he considers growth capital and finds the market uncertain.
  • He also notes that even with general tailwinds, he is also beginning to see headwinds emerge in the form of more competition in paid advertising costs and availability because of the pandemic’s tailwind effect on ecommerce and online business.

From Corey Kossack, Founder/CEO of Aspireship:

  • For Aspireship, an online learning and talent platform that helps people transition to sales careers in the SaaS industry, the pandemic initially was a “huge curveball”, having both headwind and tailwind features.
  • Suddenly, a lot more people were interested in using the pandemic period, however long it might be, to level up in their skills and explore new career opportunities. That was both a tailwind (new candidates) and a headwind (how long is this bizarro state going to last?)
  • With the headwind uncertainty, Corey chose to take the time to invest in the platform to create more value for the candidates and in doing so discovered a new revenue stream — companies are willing to pay to provide leveling up for their existing teams and increase retention of new hires!
  • I.e. the headwind condition for companies causing them to lockdown on new hires also had a tailwind that resulted from the WFH context in the form of increased demand for relevant remote training.
  • With that insight, Aspireship worked to level up the company side of its platform and effectively accelerated its entire game plan!

There’s no real moral to the story other than that it may benefit the performance of your startup to stay alert, more than usual, to your headwinds, crosswinds and tailwinds and be prepared to be nimble…… just like always.

StartupAZ Foundation

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