Entrepreneurship’s Ups and Downs

Michael Risich – Entrepreneur turned technologist, turned technology founder with an exciting journey building a SaaS business scaling to 10M in ARR with an exit to a PE firm!

Entrepreneurship’s Ups and Downs

His journey into the automotive industry began when he started teaching at a community education program to overcome his fear of public speaking and earn some extra money. One of his students happened to be a repair shop owner who expressed frustration with his business software’s limitations. Intrigued, Michael agreed to evaluate the software and discovered several flaws, such as the inability to auto-increment invoice numbers and a lack of checks and balances.

He was able to ask the right questions and understand the problems that shop owners were trying to address. Through his connection with the repair shop owner, he was introduced to other operators and business owners in the automotive industry who faced similar pain points.

These owners, who were successful entrepreneurs in their own right, saw the potential for technology to revolutionize their businesses. Michael’s ability to understand their needs and provide solutions positioned him as a valuable resource. He began working closely with these owners, refining their software to meet the specific requirements of auto repair shops.

As the small team of owners expressed a desire for the software, Michael wrote a statement of work, outlining the estimated time and cost based on hourly consulting rates. However, the owners informed him that they typically paid for software on a monthly basis, rather than a one-time fee.

To address this, Michael proposed an alternative approach. He asked each owner to introduce him to five potential customers to accelerate revenue generation. The owners agreed and facilitated introductions, which helped Michael expand the customer base.

In the early 2000s, before the popularity of SaaS subscription models, Michael had about 60 shops in the Philadelphia area paying a monthly fee to use the software. This arrangement aligned with the owners’ preferences and allowed for a more steady and predictable revenue stream. The software proved valuable to the shops’ existing systems, enhancing their efficiency and accuracy in managing their operations.

Relationships were key to enabling Michael access to resources beyond his direct control. Michael built these relationships by listening, asking questions to confirm his understanding, making commitments, and then meeting them–or letting the other party know as soon as he did that he had encountered a problem and needed to adjust course.

Bootstrapping constrained his spending, but unlike many other technical entrepreneurs who focus exclusively on coding their way out of challenges, he realized at critical points in the evolution of Bolt On that he needed to focus more on selling what he had. He would take prudent risks, placing bets that were likely to pay off but that he could afford to lose.



Staying Resilient in Entrepreneurship’s Ups and Downs

In the video below, Michael shares some strategies that helped him stay motivated and resilient during challenging times. Here are the strategies he mentioned:

  1. Having a trusted mentor: Michael emphasized the importance of having someone experienced who can provide guidance and support. A mentor or business coach can offer advice, perspective, and reassurance, helping you navigate difficult situations and stay focused on your goals.
  2. Seeking support from a loving spouse: Michael highlighted the role of a supportive spouse or partner in providing emotional support and protection during tough times. Having someone who understands your journey and encourages you can make a significant difference in maintaining your motivation.
  3. Participating in a Mastermind or Bootstrappers Breakfast roundtable group: Michael found value in surrounding himself with other entrepreneurs who faced similar challenges. These groups provide a supportive network where you can open up, seek feedback, gain strength, and receive constructive criticism. They offer both understanding and accountability.
  4. Being vulnerable and willing to ask for help: Michael emphasized the importance of being open to asking for assistance when needed. Whether it’s seeking advice from mentors, industry contacts, or your support network, being willing to ask for help is a sign of strength and can provide new insights and solutions.

By implementing these strategies, Michael was able to maintain his motivation and overcome challenging situations. It’s important to adapt these strategies to your own circumstances and find the support system and approaches that work best for you.

Full interview




Michael Risich’s Favorite Business Books


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