5 Battle-Tested Lessons from a Bootstrapped Startup

For the last 4 years, I’ve been running Hello Scheduling, an employee scheduling and time clocking company.  5 Battle-Tested Lessons from a Bootstrapped StartupOur business is 100% bootstrapped – we’ve never taken outside funding — and profitable.  Over that time period I’ve made a lot of mistakes, but I’ve learned a lot along the way.  In no particular order, here’s what I’ve learned:

1. Don’t Recreate Existing Solutions.  When you’re running a technology startup, one of your most precious resources is engineering time.  Engineers love to build things and sometimes they have a tendency to build software that already exists.  This tends to be a waste of time and resources.

Does your team really need to create your own in-product analytics tool (as an example) when mixpanel has a team focusing on this problem?  Unless the tool is absolutely critical to the core of your business, your engineers should focus their very valuable (read: expensive) time directly improving the core value your company provides.

2. Apply an Engineering Mindset to Customer Satisfaction.  There’s no mysticism when it comes to how to make customers happy. At our company, we use Net Promoter Score and ask two simple questions approximately two months after a customer has subscribed:

  1. How likely is it that you would recommend Hello Scheduling to a friend or colleague?

  2. Why did you give us that score?

From the answers we get, we follow up with customers to understand their feedback, and then work to improve our product.  Our methodical approach has led to dramatic gains in customer satisfaction and increased subscriber retention.

3. Focus on Optimizing Your Funnel. In the software world, it’s all about pouring leads in. But rather than spending money to get new leads, have you fixed your sign-up and onboarding experience? If only 80% of users are making it through your sign-up process, you need to understand why people are abandoning the process:

  • Is your sign up process too long?

  • Do users not trust your product/company?

  • Are your users running into technical issues with sign-up?

  • Do you ask for too much personal information (e.g., phone number)?

At Hello Scheduling, if a user has started the sign-up process but not completed it within 20 minutes, we send an automated email – which looks like it came from my personal inbox – to see if they ran into any issues.

Optimize your funnel before you spend a dime on getting new leads.

4. Polish Existing Features Before Building New Ones.  You won’t believe how many requests my company gets for new features, but we’ve found that the most effective way we can spend out engineering resources is on improving existing features.  We try to polish our product experience, like Apple does, rather than building a whole bunch of new features that folks won’t use, like Google or Microsoft. We’d rather be excellent at a few things than mediocre at many.

5. Businesses Buy Solutions, Not Technology.   When you’re thinking about your product messaging, do you focus heavily on features?  Stop.  Businesses doesn’t buy features; they buy solutions to their problems.

“Our employee autoscheduler has over 20 rules and checks 50 different parameters before scheduling employees.”  That’s weak, feature-driven messaging.  Always talk about your features in terms of benefits: “Our employee autoscheduler will save your managers hours per day, so that they can get back to more important things.”

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About Jon Byrum

Jon Byrum is the president and co-founder of Hello Scheduling, a provider of employee scheduling and
time clock software for small businesses. He writes regularly about his startup experience on the Hello Scheduling blog.