Top 10 Lessons From Season One of Speaker Series Rewind

Here are ten lessons from our first ten episodes of Speaker Series Rewind, a podcast featuring leaders, founders, and investors.

Article by
Katherine Martin

Sometimes the best ideas come from people beyond your everyday network or industry.

That's why we host a monthly Speaker Series, which provides a forum for industry leaders, successful entrepreneurs, and investors to share their unique perspectives with our network and the broader tech ecosystem.

Over the years, we’ve held 59 interviews and counting featuring guests from international recording artists to professional athletes and SaaS unicorn founders.

Since all of our interviews are packed with tactical advice that transcends time, we turned our archive of Speaker Series recordings into a podcast called Speaker Series Rewind. Instead of playing back the episodes in order, we’ve curated a handful of our favorite interviews together thematically, starting with Founders and CEOs. 

In 2021, we released our first ten episodes with guests, including: 

If you're new to the podcast and you're not sure which episode to listen to first, below are ten lessons from our first ten episodes: 

1. The CEO Needs To Be a Functional Supervisor 

Many first-time founders and CEOs transition from managing one department, one domain, and one function, which they likely came from. All of a sudden, they have to get their arms around all the basics of each function. If you don’t know enough about each function and how it fits with all the other functions, you can wake up and be in terrible shape one day without seeing that it’s coming.
Matt Blumberg, CEO, and Founder of Bolster

Listen to the full episode here.

2. Pay It Forward by Sharing Opportunities

We all bear responsibility. If somebody took a chance on us, make sure that when you're in a position to take a chance on somebody else that you do it.
Beth Paretta, Principal at Paretta Autosport

Listen to the full episode here.

3. Buying The Leader Always Pays Off

If you get to the size where you're making acquisitions, the one thing I will tell you is it always pays to buy the leader - every time. You can pay whatever you need to pay for the leader, and then you can screw it up as an operator. You can make bad decisions, and you still win.
Brad Rencher, CEO of BambooHR 

Listen to the full episode here.

4. Know The External Factors that Will Affect Your Business 

Something happens externally from your business that affects your business at least four times a year.  So, if you don't know something that is impacting your customer at least four times a year, then you're not in touch.
Julie Lyle, Former Walmart CMO & Founder of Zytara

Listen to the full episode here.

5. Strong Conviction Leads to Personal Fulfillment

I'm doing my best every day when I get out of bed to focus on this thing that is really important. And since I can't imagine a more important problem to work on, there's just a lot of personal fulfillment there. No matter whether the things I build their success or not.
Jason Jacobs, Founder of Runkeeper

Listen to the full episode here.

6. Focus on Making an Impact

At the end of the day, you look back on those great things that happen and make you better. The biggest joy that I've had in growing the company is that we're doing something that we think is important.
Gerry Dick, Founder of Inside INdiana Business

Listen to the full episode here

7. Control Your Destiny

We might raise more money. We might do this. Who knows! But I want to be able to control my destiny. I want to be able to choose to do those things, not be forced to.
Sahil Lavingia, Founder of Gumroad

Listen to the full episode here

8. Embracing The Chaos of Entrepreneurship 

Change and chaos are the only constant that we have. So, you have to learn to embrace that from the get-go, and you'll be so much happier in life because of that.
Dave Colt, Sun King Brewing

Listen to the full episode here

9. Don’t Forget to Take Care of Your Mental Health as an Entrepreneur

You need help on this journey. It doesn't just come together like a perfect puzzle. I see a therapist every two weeks now, and he's an important part of hopefully me being a better CEO, husband, and father.
Jeremy Swift, Founder & CEO of Cordial

Listen to the full episode here.

10. Raise Money When You Don’t Need It

I always encourage folks to always raise your money when you don't need it. A lot of times people go and raise their money when they desperately need it. You're definitely the loser in that scenario.
Angie Hicks, Founder of Angie’s List

Listen to the full episode here

You can also stay up to date on the latest episodes of Speaker Series Rewind by subscribing to the podcast wherever else you like to listen.  You can find us on Apple PodcastsSpotify, Google Podcasts, and Stitcher.

Suggested Content

Chapter IV: High Alpha’s Latest $125M Fund


To commemorate the launch of High Alpha IV, High Alpha Partner Kristian Andersen shares more about the firm’s fourth and largest fund to date.

Go to Post

XO Summit Recap: Slowing Down to Speed Up


We brought together 40+ startup founders from our portfolio for two-days of learning, networking, and inspiration.

Go to Post

Bolster CEO Matt Blumberg on Board Structure, Management, and the Power of Independent Directors


We sat down with Bolster CEO and Co-Founder Matt Blumberg to learn more about board management and the power and impact of independent directors.

Go to Post