Michael Roub

Seek challenge. The desire to learn and get exposed to new opportunities will broaden any entrepreneur’s skillset and enhance their knowledge.


Michael Roub has spent the past two decades providing strategic direction and leadership to clients, business owners and management. Michael started Inflection 360 to provide hands-on, collaborative consulting to management teams, primarily in small to medium-sized businesses.

Prior to starting Inflection 360, Michael held executive positions with multiple healthcare companies. He was VP of Business Development focused on acquisitions at each of U.S. HealthWorks and Western Dental. Michael also led operations and new site development for a multi-specialty surgical center business which was acquired by a public company.

Michael began his career in investment banking where he worked with numerous major corporate clients on equity and debt capital raising, mergers and acquisitions, and corporate restructuring engagements. Michael also was VP of Finance at a Silicon Valley start-up prior to entering the healthcare sector in 2002.

Michael earned a BS in Economics from the Wharton School of Business at the University of Pennsylvania and an MBA from the University of Chicago Booth School of Business.

Michael currently lives in Los Angeles with his wife of 20+ years and their two teenage children. Michael actively volunteers and in recent years has been particularly involved with the University of Pennsylvania as an alumni interviewer for applicants, as a volunteer and fundraiser for Making Strides Against Breast Cancer, and as a board member for the local high school and youth lacrosse programs. Travel, sports and fitness are passions for the entire Roub family.

Where did the idea for Inflection 360 come from?

When I was acquiring healthcare practices for Western Dental Services and US HealthWorks I consistently found that the practice owners were leaving money on the table. Few owners were well prepared to sell their business. Their advisors, if they had any, failed to have them put in the extra work to make their business stand out amongst competitors. I realized that these owners would benefit significantly from working with a team that had been on the buy side of so many transactions. Effectively, I wanted to level the playing field for the small business and healthcare practice owner when selling to a larger competitor or a financial sponsor.

What does your typical day look like and how do you make it productive?

I start at least three days each week with a 6:30 workout at Orange Theory Fitness to stay mentally and physically fit. Once I sit down to start my work day, I review my to do list which I prepared the evening before to make sure I have my priorities in order. I then spend no more than 30 minutes with emails before moving on to morning calls or meetings. I will again read emails for 30 minutes at midday. I try to use the afternoons for focused client work. While I work long hours most days, I always make sure that at least a few hours each evening are focused on family. By trying to keep a reasonably consistent schedule, I am able to stay focused and productive.

How do you bring ideas to life?

My objective is to approach each consulting relationship as a collaboration. I look to learn from the management team’s experience to help move their most critical objectives forward. Since successful outcomes require a tremendous amount of effort and work, my firm Inflection 360 has a roll-up your sleeves mentality. We don’t just give advice, we make it actionable.

What’s one trend that excites you?

Organic and natural food prevalence. This trend is exciting both from a business perspective as well as from a personal one. My wife is a cancer survivor, and having the cleanest diet possible is paramount for her. It was more challenging even just a few years ago to have a wide variety of organic options. However, now particularly in Los Angeles where we live, the options for organic foods in groceries and restaurants seem endless. Clearly, budding entrepreneurs have seized an opportunity to develop market niches and the successes of many of these businesses has been exciting to watch.

What is one habit of yours that makes you more productive as an entrepreneur?

Each evening I take 15 minutes to plan my highest priority tasks for the next day. This allows me to both reflect on what happened during the day and also to start the next day with a focused game plan. While few days go as scheduled, I am much more productive due to my prior evening planning.

What advice would you give your younger self?

Life’s challenges will be so much greater than you could have ever expected. However, know that you will make it through each challenge and be stronger for it. Don’t be afraid of failure or doubts from others. If you have the love and support of your family, you will persevere and be successful.

Tell us something that’s true that almost nobody agrees with you on.

The customer isn’t always right and it’s ok to let them know. I get paid for my expertise and advice. Typically, my goal is to have a client meet or surpass their business objectives. However, at times and at the risk of alienating a client, a misguided client needs an objective voice to send them down the right path. While I don’t seek areas of disagreement with clients, my primary goal is their ultimate success. It can take some planning and finesse, but most clients ultimately appreciate when you are able to demonstrate where they are mistaken if it will lead to positive returns.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Seek challenge. Whether taking on new types of engagements, working in different industries or making complete role changes, I am always seeking the next challenge. The desire to learn and get exposed to new opportunities will broaden any entrepreneur’s skillset and enhance their knowledge.

What is one strategy that has helped you grow your business?

Create valuable opportunities for others. I have introduced numerous individuals, accountants, investment bankers, real estate investors, etc. to other individuals where I felt they could provide value. No deals, no referral fees, just creating value for others. This in turn has led others to look to me and my firm for guidance and to involve us in opportunities with their existing client base. The more I can help others be successful, the more successful I have become.

What is one failure you had as an entrepreneur, and how did you overcome it?

I initially underestimated the need to develop a marketing platform. I had a large network and was able to source multiple clients from that base of relationships. However, in time, I needed to expand my reach and develop a stronger online marketing presence. While I spent a lot of time reviewing marketing platforms, I was fortunately introduced to the team at Branding Fast (www.brandingfast.com) which took a very focused and personal approach to helping Inflection 360 grow. Their team provided the knowledge I lacked in digital marketing.

What is one business idea that you’re willing to give away to our readers?

While I have seen some examples to solve this problem, too few night spots, particularly on college campuses have coat checks (particularly relevant in the Midwest and Northeast). A mobile coat check business could easily operate outside of popular night spots and provide a secure and efficient way to keep students warm in winter months without the risk of having their coat stolen or damaged. It would have been great for me during college in Philadelphia.

What is the best $100 you recently spent? What and why?

It was actually $100+ x 2. I took my daughter to Disneyland for the day. She is 16, not a little girl anymore, and life is busy. For the two of us to have a day where we just went on a ton of rides, talked and laughed was incredible. Life is so busy, taking a day to be with just her was so important and memorable.

What is one piece of software or a web service that helps you be productive? How do you use it?

I have used LinkedIn obsessively over the past decade. While not all connections prove significant, I have been able to connect with others that have led to multiple business relationships including some acquisitions. When I am trying to gain exposure to a particular industry, I always start with my LinkedIn network to see who can share some knowledge or experience.

What is the one book that you recommend our community should read and why?

Randy Pausch’s The Last Lecture. Everyone should pick up this book and re-read it every few years. Randy’s words will help remind you of what is truly important in life. It will make you laugh, cry and rebalance priorities.

What is your favorite quote?

We have all faced adversity, but this quote from Martin Luther King, Jr. stands out: “The ultimate measure of a man is not where he stands in moments of comfort and convenience, but where he stands at times of challenge and controversy.

Key learnings:

• A consistent daily schedule will lead to a focused and productive day. It will also allow for personal priorities (i.e. time with family) to be part of your day.
• 15 minutes of evening preparation for the day ahead allows for both (i) reflection on the previous day’s successes and opportunities, and (ii) a focused jump start for necessary tasks the next morning.
• Helping others connect with potential business opportunities without any demands or expectations of compensation or consideration can actually create some of the most valuable long-term relationships and future client pipelines.
• Read or Re-read The Last Lecture by Randy Pausch to help put life’s priorities in balance.


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