The Secrets to Bootstrapping a Business: Gule Sheikh Shares her Experience

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Show Notes:

Bootstrapping a business is often considered a necessary evil especially when starting a business. But have you ever wondered why? And how you overcome it? Our guest today will clear everything up for you.

Gulé Sheikh is a healthcare technology strategist and a successful former entrepreneur. She founded a health tech company, scaled it by 1000%, and exited after 7 years of running it. Gulé was interviewed by Melinda Gates as one of the few health-tech startup owners that raised over $2MM in Capital in the Mid-West.

With over 23 years of experience in technology and in 12 years in healthcare, she is very passionate about health IT innovations, innovation strategy, and solving healthcare problems. Gulé has been bridging the gap between healthcare and technology with her innovative thinking, business-oriented mindset, and can-do attitude.

According to Gulé, successful entrepreneurs always go the extra mile. If you want your company to thrive, you need to put extra effort into everything you do.

In this episode of the Think Business with Tyler podcast, we talk about how to deal with self-doubt and fear of the unknown as an entrepreneur, the pros and cons of bootstrapping a business, the importance of relying on data when making business decisions and why you need to go the extra mile to thrive in business.

If you want to learn more about a rewarding yet risky thing called entrepreneurship, tune into this episode to find out.


💡 Name: Gulé Sheikh

💡 What she does: She’s a Healthcare Technology Strategist and a successful former Entrepreneur of a health tech software.

💡 Noteworthy: Gulé successfully Co-Founded, venture-funded, and exited a health-tech company. She has 22+ years of experience in the IT industry servicing clients in health care, financial services, and the public sector.

💡 Key Quote: “Think big. Surround yourself with people who have achieved a lot more and ask for help whenever you need it.”

💡 Where to find Gulé: LinkedIn

Key Insights

How to deal with self-doubt and fear of the unknown as an entrepreneur? Entrepreneurship is highly rewarding but also highly risky. If you’re a business owner, you’re probably familiar with the overwhelming feelings of inadequacy, self-doubt, and burnout. The trick is to push through those challenging moments and always have in mind why you started your business in the first place.

Gulé says she’s no stranger to entrepreneurial self-doubt. She shares some tips for overcoming it. “Every single day I question myself. Every single day, I went to bed at night thinking what am I doing? Is this going to work?

I have no idea what’s going to happen and every single day I woke up in the morning, I was like my feet on the ground. I’m just like, we’re gonna get this, I know what I’m doing. There was just something inside of me where I was just pushing so hard and I really felt that this was going to change the industry.”

Bootstrapping is both an empowering and limiting way of growing a company. Bootstrapping is often considered a road less traveled in the business world. There are so many things that come when you’re bootstrapping a company, from lack of networking to slow growth. However, self-funding a business is not always that bad. As Gulé points out, even though there’s a huge personal risk, at the end of the day, you’re your own boss.

She says, “The one thing with bootstrapping is you’re definitely limited in terms of how fast you can scale and what you can get done because you have to be extremely frugal, extremely scrappy, and very resourceful and you have to know where to look. And that can take time to get that done. So it takes you longer to scale versus having the funds available to you and having a solid team in place.”

Data is key for making informed business decisions. It’s a tale as old as times: you need to rely on data to make better-informed decisions for your business. As much as you think you know your customers to the core, it’s better to be safe than sorry. Listen to what the data is telling you because you might be surprised about the results.

Gulé shares, “That data then helped us look into understanding why the patients weren’t picking up their medications. And then we realized that actually, this is a whole industry-wide problem where 50% of the population don’t pick up their medications. And the majority of the reasons around that is because of cost. […] So it was just it was all taking that data in and developing the right insights and understanding industry-wide and comparing it to research and population health data to understand what was really going on.”

Always go the extra mile. As a founder, you need to be ready to go the extra mile, especially if you want to stand out from your competitors. Whether that’s when you’re interacting with your customers or presenting a project to your board, you will not go wrong if you put in some extra effort.

Gulé explains, “It was definitely the extra mile with the entrepreneurial side of things. And the way I think is just you’re never going to go wrong in any situation if you are over-prepared. So the more information you have, the more research you have done, it will show. Even if you don’t have to use that information, it will show in terms of your knowledge, your passion, your focus, your drive, your discipline, and understanding the full picture of what you are coming forward with.”

Top Quotes

“When you have your own company, you have to think about the things that you don’t always have to think about. So having a good amount of money set aside for you for that rainy day as they call it. The unknown of, are you going to get customers? Are you going to get enough paying customers? How long will this take you to scale? How scrappy do you have to get? Just a lot of fears. Will people take you seriously? Will you be able to raise money or not? So I would say there was just a lot of fear of the unknown of what could go wrong but then also being optimistic enough to still move forward.”

“At the time when I was bootstrapping, the pros I was thinking was I have control over my company so all the decisions I made from a technology standpoint, from a design standpoint, from a customer experience standpoint, I can control what that looks like and I don’t have outside forces telling me to do otherwise where I’m so close to the customer and their needs.”

“I think every single aspect of your product wherever you are, whether it is you’re building your product or the end-user and their experience of your product, you need to have data to rely on to make the right decision.”

“It was a hard grind for a good seven, eight years. And then when it came to wrapping up it was very mixed emotions because I basically developed this company as well as raised my child at the same time. And I still strongly believe in the product that I created.”

“There were challenges, though, in terms of showing up at the table where I felt and sensed that I if I wasn’t over-prepared, or if I didn’t go the extra mile to prepare for either my board decks or my pitch information and the background, that it would not be taken as seriously as if we weren’t as well prepared.”



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