In this episode #25, we are talking with Bridget Harris, the co-founder of YouCanBook.Me (, an online appointment schedule which works directly with Google, iCloud and Microsoft cloud calendars. Some founders are drawn to the opportunity to raise millions and get yet another validation from investors, as well as a chance to grow really fast to beat the market. Others only consider bootstrapping for the sake of being completely independent and having full control over their business. Bridget Harris from YouCanBookMe talks about the way they bootstrapped the company to $5M ARR and are planning to double that in the next couple of years. They’ve got a great set of values that drive YouCanBook.Me forward, and it definitely looks like this kind of growth is possible for them!

(0:00:07) – Building a Successful Online Scheduling Tool 

I chat with Bridget Harris, the CEO and co-founder of YouCanBookMe, an online scheduling tool that helps businesses manage their customers and calendars, and advocate for balanced and transparent remote communication. Bridget’s journey from politics to business, and how she and her co-founder Keith made the decision to make a difference in building a company are discussed. We look at how they built the YouCanBookMe app, which had customer growth and product market fit. We also discuss the transformation of technology over the last 20 years, and how they have been persisting to make their business a success.

(0:10:54) – Bootstrapping vs. Funding for Startups 

We explore the entrepreneurial journey of Bridget Harris, the CEO and co-founder of You Can Book Me, and how she chose to bootstrap the business rather than seek investors. We discuss the concept of ‘ramen profitability’, and how she and her co-founder had to manage their resources carefully in order to stay afloat. We also consider when to consider taking money from investors and what mindset shift is required when doing so. Finally, we look at the difference between a desire to be “king” or “rich” when it comes to bootstrapping a business.

(0:17:49) – Bootstrapping and Prioritizing Company Spending 

Bridget Harris’ entrepreneurial journey and her decision to bootstrap her business rather than seek outside funding are explored. The advantages of staying independent, such as having more control, are weighed against the potential to make more money with larger companies. The importance of hiring the right people for your business and how to be frugal in order to make the most out of your resources are discussed. Finally, Bridget’s thoughts on what she would never be frugal about and how to adopt the right mindset to make the most of what you have are explored.

(0:32:28) – Value-Based Spending in Business Leadership 

We discuss the importance of laptops for employees and how to approach purchasing them. We also touch on the importance of budgeting for travel expenses and recognizing the value of spending money to protect or grow the company’s assets. Finally, I share my experience as a first-time CEO and how I’ve navigated the journey of running a business.

(0:39:23) – Balancing Hands-on Operations and Strategic Leadership 

We explore the world of company culture, values, and high-performing problem solvers, and how they all intertwine. We emphasize the importance of having a balance between having a tight set of policies and procedures and allowing for soft diplomacy that encourages ownership over the work that people do. I also reflect on the most painful thing about being a CEO of a company – when we let people down – and how to minimize that pain. 

(0:46:54) – AI’s Impact on Knowledge & Business

We tackle the importance of building a successful business with a strong relationship with customers, and the satisfaction that it brings. We discuss the role of failure in running a business and the importance of not trying to build bespoke software solutions. We also explore the importance of integrating the best tools and systems and discuss the trend that will have the biggest effect on the future.

We explore the future of humanity and the potential for technology to both help and hinder our progress. We examine how AI can propel us to a new era of innovation, but also how it can be used to harm us if put in the wrong hands. 

Head of Growth,