Being Small Is a Benefit: How to Leverage Being a Bootstrapper

Reading Time: 6 minutes

Many founders feel they need to act bigger than they are. They expect only to be taken seriously when they appear to be a mature company. It turns out that this is no longer the case in many industries.

Depending on the size of your customers, the fact that you are a small business with barely any employees, if any, can be incredibly useful. If you are selling to individual customers or are in a B2BC market where your customers are tiny companies or freelancers, the fact that you’re not just another faceless corporate entity will be a most welcome surprise. People treat you differently when you show that you’re in the market because you care.

At FeedbackPanda, we communicated clearly from the beginning that it was just Danielle and me running the company. Our customers even took up the work of correcting other people public when they assumed we were a larger business. That always kept the founders relatable. We were just like our customers, real people solving real problems. This kind of relationship allowed us to mess up from time to time, only to encounter a lot of goodwill and understanding.

Bootstrapped founders and their businesses are different from other enterprises in a few key ways, and each of those can be used to your maximum advantage.

Bootstrappers have skin in the game. They can’t hide behind a corporate facade. Reputation is important to them and the success of their businesses. Customers understand that once they are dealing with a bootstrapped, they can expect more than “business as usual.”

If you’re selling to a niche that understands the bootstrapping life, such as the startup market, you will also encounter this behavior. In the end, it boils down to honesty. Can you reliably deliver the levels of service that your customers expect? If you explain from the beginning that you being a solopreneur might mean that the service can be shaky when you’re not there to fix it, you will allow your prospects to pre-sort themselves. You wouldn’t want to have a customer you can not yet serve anyway. Once the business enters the Stability Stage, you can change your messaging to attract those customers.

Leverage having skin in the game like this:

• Be clear about being a bootstrapper whenever you think a customer overestimates the size of your business. Don’t go for sympathy; go for comprehension. When a customer complains about a bug, don’t say, “It’s just me, this will take a while”, instead tell them that you’ll personally get on it right after the conversation. Convey that their direct feedback matters.

• Appeal to Early Adopters by using their language. In the early stages of your journey, using labels like “pre-release,” “beta,” and “prototype” will attract innovators and Early Adopters while it will keep mainstream customers at bay. 

• Be public about your journey. Talk to other founders, no matter if they are your audience or not. Share your story, leave traces. People who care to find them will follow your journey and support you because they know how important this is for you. They will respond to your questions when you need an external perspective, and they will spread information about your journey to those who will listen.

Bootstrappers have nothing to lose. We don’t have insane amounts of capital. We don’t have hordes of employees we need to employ securely. We are flexible and can adapt to changing circumstances in the industry we serve much faster than established companies that cling to the status quo. If a prospect chooses your service, they can be assured that you will do whatever it takes to keep making your product better at solving their critical problems.

Leverage having nothing to lose like this:

• Show the journey of your product proudly. Document and publish the evolution of your product, your business, and your entrepreneurial perspective.

• Celebrate features, pivots, and improvements. Blog about things that make a difference in your customers’ lives, and be proud of it. Your agility is your advantage. Communicate this with your prospects.

Bootstrappers have everything to lose. While our agility makes us very adaptable, it also prohibits us from entrenching ourselves too much: other bootstrapped businesses might just spring up and start competing with us. For that reason, we’re forced to build as stable and reliable a business as possible. For many founders, that means dedicating every minute of their day to their product and its customers. If a prospect chooses to buy from you, they can expect you to work your hardest to get and retain their business.

Leverage having everything to lose like this:

• Celebrate your challenges. Don’t hide the bad and only talk about the good. Share what worked and what didn’t with the founder community. Customers will do their research, and when they find that you work hard on finding the best way to go forward, that will create a lot of goodwill.

• Share your struggles and growth as an entrepreneur. You don’t have a gigantic safety cushion and utopian exit bonuses when you leave the business. If your business fails, so will you. By showing how you deal with problems and reliably overcome them, you’re projecting confidence and that you’re in it for the long run.

Bootstrappers are laser-focused experts. One consequence of having access to very little capital and no employees in the beginning is that a bootstrapped business usually solves one thing really well and nothing else. For that, the founders have to be or become experts in their fields. When your prospects see your business, they don’t see a giant corporation with dozens of unrelated product that they’re trying to force on every possible customer, whether they need it or not. They see a purpose-built business that is working tirelessly on offering a product that solves a critical problem for a well-defined audience, with a founder that knows what they are doing. 

Leverage being a laser-focused expert like this:

• Show your expertise by writing. Have a blog, write regularly, and write about what you know. Be a voice in your niche audience that people will follow.

• Get interviewed on podcasts. Nothing shows your expertise level more than a fruitful discussion with another expert in the industry you serve. Promote the episodes when they get released with your audience.

Bootstrappers are steering the ship. It is that founder that not only envisioned the business, but they are operating and improving it every day. Often, a customer reaching out to customer service will be talking to the founder of the company. Unline a rank-and-file employee at a large faceless corporation, the founder will pour their heart into every single interaction with a customer, and they will notice the dedication and attention they were shown. You can use your direct connection with customers to turn a stressful customer service chat into a delightful trust-building opportunity. 

Leverage steering the ship like this:

• Be present and empathetic every time you talk to a prospect or a customer. A great customer service interaction will stay on people’s minds for a long time, and they will talk about it to their peers.

• When interacting with partners and large customers, you, as the founder, can use your command of the business as a credible argument as to why you can guarantee certain things. No confirmations and verifications needed when you’re the one both promising and delivering things.

Bootstrappers are relatable. In most families, you can find an entrepreneur. It’s a grandfather who was laid off from a job in the factory and started his own business. It’s an aunt who decided to turn a hobby into a business and is now employing a handful of people. We all know someone, a relationship or an acquaintance, who decided to start their own thing. Your customers will too. By making it clear that you are a person running a business, their expectations and capacity for understanding will increase significantly. In a way, you are an underdog, just like their dad was when he started the family business. You’re someone who cares, like their sister-in-law, when she quit her high-paid-but-unfulfilling office job to start a project that helped real people with real problems. 

Leverage this level of relatability like this:

• Prominently show the person behind the business, directly on your landing page or in an about page. Make the business about yourself, use your personal brand and motivation to be more relatable.

• Share the origin story of the business both through your business communication and outside of it, in interviews and on social media. People love narratives, and nothing is more attractive than a rags-to-riches underdog story in the making.

• When interacting with your customers, use a real-life picture for your user avatar and use your full name. Engage with people on a personal level, as the engaged founder, not the distant business owner.

Use your agility and nimbleness as a bootstrapper to your advantage. Present yourself to the world as a real person, with all the shortcomings and problems that every one of your customers encounters in their own lives.

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