Anyone can refine their leadership skills. (BCV)

How To Be an Inspirational Leader

The ability to inspire is not the same thing as charisma, and if you want to help your startup grow, there are approaches you should practice.

8 min read November 8, 2023
The Head Start The Head Start Running Your Company Early

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The thing that the best and brightest entrepreneurs have in common is their ability to inspire – their customers, employees and investors.

I’ve worked with top-tier founders like Marc Lore of Jet (sold to Walmart for $3.3 billion in 2016), Brian Long of Attentive (valued in 2021 at over $11 billion) and Jennifer Hyman of Rent the Runway (went public in 2021), who share this power, and they leave all their key stakeholders as excited as they are to tackle their markets.

It’s a common misconception that this ability to inspire is the same thing as charisma. There are many examples of people who are popular and well-liked but lack the ability to rally those around them around a common mission.

For startup founders, particularly in the early stages, the ability to inspire has everything to do with the ability to get others to see the world the way you do. Generally speaking, that means not only articulating a compelling vision of the future that includes a problem you’re trying to solve, but also clearly laying out the concrete gameplan for how you’re going to get there. 

This is why inspirational leadership can make all the difference to your early-stage startup, and it’s important to note that it is something to practice, rather than a trait only inherent in some people. In this piece, I’ll explore ways this skill applies to all aspects of company-building, and share insights into how any founder, regardless of personality, can develop this skill for themselves.

Practice articulating your vision

More than anything, the ability to inspire comes from your own conviction – in your own mission and vision. Often, figuring out that vision is less a matter of creation and more an act of remembering: What was the thing that drew you to the life of an entrepreneur in the first place? What’s the singular problem in the universe you believe that you and your team are uniquely capable of solving? 

Once you can clearly and concisely articulate both that problem and your solution, you need to work on the ability to get other people as fired up about the mission as you are. Founders should practice describing their vision in a clear and succinct way, getting their stakeholders to see a future that doesn’t yet exist. It’s a matter of selling not only your mission, but also your confidence in achieving it. 

This ability to inspire plays a key role in recruiting, particularly for early-stage startups. Much like Steve Jobs’ legendary call to arms to Pepsi’s John Sculley, your ability to recruit the talent you need hinges largely on whether you can get them as excited for the opportunity as you are.

Take it from me: In my own career as an entrepreneur, as co-founder of ProfitLogic, my co-founder and I were faced with a scenario where we were actively scouting an engineer right before his graduation from Harvard’s computer science program. The problem was that he had three other very lucrative offers on the table from brand name outfits, including Microsoft. 

We couldn’t match those other offers in terms of cash. We could, naturally, offer equity in the company as part of the compensation package, but you’re still asking the candidate to take a risk that the startup will take off and those shares will be worth something.

The way we won him over wasn’t by trying to convince him that the equity in our company might be worth more than Microsoft was offering him, but rather by talking candidly and openly about our business and ourselves – our hopes and dreams for the company, why we chose to take this risk, how we arrived at this specific method of solving this specific problem. It turns out he ultimately found the mission as inspiring as we did, and he wound up being a critical member of the team for many years.

Note too that communicating your conviction in the mission isn’t just about hiring – it matters even after your team is in place. Startups go through ups and downs, and a strong mission, one that the founders are clearly behind, can help keep employees motivated and focused, especially when times are tough.

Know your audience

As with early investors and key hires, winning over customers as an early-stage startup is less about pitching a product, and more about selling them on your vision.

When Brian Long and Andrew Jones at Attentive went out to find their first customers for what was an innovative new SMS-based marketing platform, they were long on vision but short on product. But that didn’t stop this dynamic duo from convincing a dozen early customers from testing out the idea, buying into not only the efficacy of the product in its early state but importantly the vision Brian and AJ outlined for where it was headed. 

It’s a given that practically any young company isn’t going to have a product as complete, or a marketing budget as robust, as the tech titans. Instead, it behooves founders to inspire those customers into action: Actively listen to their needs, do your homework to make sure you thoroughly understand their particular pain point, and don’t be afraid to roll up your sleeves and work closely alongside them to figure it out. Brian and AJ were masters at this customer-centric approach and it led to a ton of early adoption and successful use. 

If customers believe in what you’re doing – in where you’re headed and why –  they’re much more likely to be willing to experiment in lockstep with your team, in the name of solving a real problem, jointly. These customers are hard to find for an early-stage company but worth the investment in the search. Not only do you find a customer, you also get the kind of real-time usage data and insight your competitors can only dream about.

Keep developing your expertise and learn how to communicate it

There’s an old chestnut that venture capitalists don’t invest in products, they invest in people. This is as true as it ever was, particularly when looking at early-stage companies. 

Much like with customers, investors want to come away feeling inspired that the founders have a firm grasp not only on the market they’re trying to chase (or create), but the problem they’re trying to solve. Products can iterate and evolve, and startups can pivot, but none of it means anything if the founders don’t have a very firm idea of what they’re trying to accomplish. 

Importantly, the best founders also inspire confidence in investors by showing a deep mastery of every aspect of their business. In the early days of Rent the Runway, while Jennifer Hyman was highly talented at communicating a vision of the future where women could have a “closet in the cloud,” she was also extremely deep into the details of how to bring this vision to reality. For example, Jennifer knew as much or more about the operations of the business, the logistics of storing and shipping clothes, than anyone else at the company. That deep knowledge of the business demonstrated her passion and her depth, inspiring confidence in us as potential investors. 

Similarly, when Marc Lore was getting Jet off the ground, his encyclopedic knowledge of not only his own company, but also the larger e-commerce and retail industries, convinced investors that he had the vision to lead the company to lofty heights. Whether it comes from doing a lot of reading, talking to customers, or both, the more time you invest in truly wrapping your head around what you’re trying to accomplish, the more you’ll be able to inspire the people around you with your deep knowledge and subject matter expertise.

Ultimately, the lesson here is that while not everybody is fortunate enough to be naturally charismatic, there are things you can do to make your leadership style more inspirational. From refining your mission and vision, to brushing up on the inner workings of the industries you’re trying to disrupt, your passion and knowledge can and will inspire those around you.

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