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Accounting & Audit

Rachel Gregg, CPA – 2016 20 Under 40 Superstars Honoree

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Rachel Gregg, CPA

Co-Founder, Managing Partner
regroupTAX / Lolana CPAs
San Diego, CA



Aside from the accounting websites, which blog/website do you consider a must-read?

TechCrunch gets me every time. The website is all about profiling startups, reviewing new internet products, and breaking tech news. My favorite part is its sister website where you can search for tech based companies and find information about their founders, funding rounds, advisory boards, etc. There are so many interesting people in the tech world and I love putting the “who, what, how” puzzle together. I’ve even seen some accountants listed on the site…who knew!

Oh, and of course


In what ways do you participate in the professional community to change/improve the accounting profession?

My co-founder, Emily Dear, and I started a San Diego based group called Future Leader Forum focused on bringing CPAs together to collaborate, share, and inspire. We are true believers in collaboration and think it plays an integral part to the success of the accounting industry.   It’s been humbling to connect some of the smartest accountants we know and at the end of the day we’ve formed some unexpected and awesome friendships along the way.

I am also on the Board of Directors for the San Diego Chapter of CalCPA. It’s a new role and I’m excited to become more involved.


What changes do you foresee in the accounting profession of the near future (3-5 years)?

I expect that as a result of technology the accounting industry will in some ways co-merge and become “flat” over the next few years. Large firms that have traditionally offered tax and write-up work will expand their services to include bookkeeping, capitalizing on higher margins created by cloud accounting tech. On the other side of the spectrum, new bookkeeping firms will continue to enter the market led by savvy entrepreneurs without specific accounting backgrounds. Currently, these new bookkeeping firms rely on the larger firms/traditional accountants for tax compliance work. However, I believe that technology will change that sooner rather than later.

It will be exciting to see if each of these types of firms will introduce their “new” products successfully and offer A to Z accounting and tax services or if they will divide and conquer, continuing to complement one another. Overall, I think technology is forcing all of us to wake up and smell the roses, reevaluate our business models and change our strategy. As a result 2020 will look very different.


How do you see yourself participating in shaping the future of the accounting profession?

I’ve always been passionate about finding ways to improve processes. As an intern at a local law firm (nerd alert) I would get so excited to start a massive copy job or scan and organize a thousand page document because it gave me a chance to create an efficient system and execute.

I hope I can continue to develop processes and products that give accountants “a better way” ultimately allowing us to better serve our clients.


What is your career philosophy?

Try to balance. Occasionally take a breath. Execute. Enjoy the journey.


Describe one person who has been an important mentor to you and how that person helped change your life.

I know this is totally corny, but my co-founder Emily Dear is one of my biggest mentors. She is such a rock. No matter what comes her way she always approaches life with certainty and determination. I am so grateful to be on this journey of entrepreneurship with her.



Learn more about this year’s 20 Under 40 Superstars, and 40 Under 40 Honorees.