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Thank you to the 1,400 leaders who’ve generously done the 7 questions!
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helps you in your leadership.



Jonno White

7 Questions with Matthew Rolnick
7 Questions with Matthew Rolnick

Name: Matthew Rolnick

Current title: VP Strategy & Innovation

Current organisation: Yaymaker

Innovative sales leader that helps companies create virtual and in-venue events (from 10 people - 10,000) to engage employees and/or entertain clients. My forte is helping create “memorable and special” events. Adding “YAY” to companies with Variety Acts, Paint Nites, Game Shows, Celebrity Pop-Ins, Comedians, Magicians, Ted Talk Speakers, Cooking Classes, Ukulele Making Classes, Wine Tasting Classes, Mixology Classes and so much more. Love networking and brainstorming creative ideas to help CEOs, VPs, HR professionals, Sales Leaders and other Team Leaders. Also enjoy networking with VCs, Private Equity and Angel Investors. Self proclaimed “King of Puns”.

7 Questions with Matthew Rolnick

1. What have you found most challenging as a leader of a small or medium enterprise?

The biggest challenge was rebuilding through the pandemic. All of our revenues were previously from in-venue events. We had to pivot to virtual events and adapt quickly.

2. How did you become a leader of an SME? Can you please briefly tell the story?

I reached out to the Co-Founder Dan Hermann. He was going through tremendous challenges once COVID hit. I continued to share support and ideas. When he saw this new challenge as an opportunity (and how I can help), he made me a VP and we were off to the races.

3. How do you structure your work days from waking up to going to sleep?

I start my day by looking through the meetings I have scheduled. I make sure I am properly prepared for each meeting (researching the company and whoever will be on the call). I am juggling several initiatives so I am constantly in meetings and helping with new strategic partnerships. From 8am to 5pm - I am often back to back to back meetings. I try to carve out at least two 30 minute blocks each day to re-prioritize and make sure I am caught up. From 5pm-9pm - I try to minimize distractions to spend with my wife and daughter (and our 3 dogs). Often from 9-10pm I hop back on my computer to prepare for the next day and upcoming week.

4. What's the most recent significant leadership lesson you've learned?

To collaborate and get feedback from other departments before presenting new big ideas. Projects will go much smoother and grow to new levels if other departments are excited about it and it can align with their goals and initiatives.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

I read the biography Hamilton by Ron Chernow (I also loved his biographies on Washington and Grant). However, Hamilton really spoke to me. It inspired me to not throw away my shot and tap more into my passion, to write more and lead by example.

6. How do you build leadership capacity in an SME?

I think it is a combination of trust, communication and setting up a structure in which people focus on their unique and core strengths. Trust must be earned and it is important to practice what you preach. Communication is an on-going work in process. However, everyone has unique strengths and I believe the best way to build leadership capacity is to tap into yours and encourage others to discover and tap into their key strengths.

7. What is one meaningful story that comes to mind from your time as a leader of an SME so far?

I think it's important to have a company focus first. I started as Yaymaker's VP of Sales but recruited a previous boss/friend of mine named Cliff Ryan because I knew how talented he was and how well we work together. I also knew he could help accelerate Yaymaker's growth. Instead of feeling threatened by Cliff, I collaborated with him. He eventually grew to the VP of Sales role, while I developed into a VP of Strategy & Innovation position. By collaborating instead of competing with Cliff, we both brought out the best in each other and helped Yaymaker break through a difficult transition. But the moral of the story is to believe in yourself, believe in others and do what's best for the business.

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