Think Like an Owner

Think Like an Owner


This show seeks out conversations with business owners and private investors to learn how to acquire and run small companies, with a special focus on search funds, micro private equity, and permanent capital. Episodes released weekly. Learn more at

I’m very excited to share that starting today Think Like An Owner will now be publishing episodes twice per week. This change coincides with our decision to close the Operators Handbook and move those topic-specific conversations to the podcast for Thursday morning episodes. You can expect these episodes to focus on topics like sales, culture, hiring, debt, capital allocation, leadership, board meetings, and dozens of other topics. This is an addition I’ve wanted to make for a long time, and I finally feel like the podcast is ready to go to this next level towards our endless pursuit of better in small business.

The second episode also means we have more availability to partner with great companies serving operators and investors through podcast sponsorships. If you’re interested, please send me an email at or connect with me on Twitter or our website I’d love to chat.

Jessica Markowitz, President and COO at Paragon Legal, kicks off our new topic-specific episodes. Paragon offers outsourced legal services to corporate legal departments, which Jessica and her partner Trista Angele acquired in 2018. Our conversation covers all things culture, including defining culture, maintaining and enforcing culture, and how to build a culture in a remote-first company. Enjoy.

Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn.


Jessica Markowitz on LinkedIn

Paragon Legal


(2:58) – What is the purpose of Paragon Legal?

(5:10) – What values do you view as incomplete and what are some complete ones?

(9:47) – Is there one value that you see as most difficult to live out?

(11:55) – What are some of the most recent adjustments you’ve made to Paragon’s values?

(13:31) – How do you sus out whether someone will live out your values in the interviewing and onboarding process?

(16:42) – Do you have some way to quantify an employee’s alignment with values during performance reviews?

(17:54) – How do you maintain and communicate values to the team?

(19:33) – Have there been any particular challenges with enforcing values?

(23:03) – How have you approached building a culture in a remote-natured company?

(29:07) – What are you considering adding or changing concerning communication or trust building?

(30:20) – How do you approach a situation where a team member is continuously not living up to the Paragon values?

(31:59) – What are some other benefits you’ve seen from focusing so much on values and culture?

(34:04) – Have you found any way to accelerate the process of building trust with a new employee to be open and honest with management?

(37:38) – Do you view the act of building a strong culture allows you to trust your team much easier in terms of delegation?

(39:30) – Where are you focusing on improving right now in terms of culture?

(43:05) – Do you have a strongly held belief you’ve changed your mind on?

(44:02) – What’s the best business you’ve ever seen?

Recent Episodes

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