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How do you scale a home service business to a 9-figure valuation in record time? In this episode of Let’s Vent Podcast, we sit down with Tim O’Reilly, the CEO of Guild Garage Group, to share his professional journey from a CPA at UCF to the CEO of a massive private equity-backed powerhouse.

Tim reveals the "Language of Business" that allowed him to transition from auditing to leading, and the specific leadership framework he used to achieve in 11 months what takes most companies 5 years. If you want to understand the intersection of high-level finance and boots-on-the-ground service, this is the episode you were waiting for.

Inside the Episode you will learn:

• The CPA Edge: Why accounting is the ultimate foundation for any CEO.

• The $1.1B Lesson: What Tim learned working with Arnie Bellini and the ConnectWise exit.

• The 5 Pillars of Relationship Leadership: Trust, Listening, Respect, Influence, and Caring.

• The "Triple Eight" Rule: How Tim manages a 9-figure empire while protecting family time and personal growth.

• How to create The blueprint for scaling home services through private equity and strategic partnerships.

Connect with Tim & Guild Garage Group:

LinkedIn: https://www.linkedin.com/in/toreilly/

Timestamps:

1:30 - How an accountant from Orlando became the CEO of one of the fastest-growing garage door companies in the world?

7:54 - The importance of relationships and How can they build you up

9:11 - Even successful businesses have many things that can be transformed.

13:54 - The value of culture.

15:27 - Easy decisions are a distractions

18:36 - How to create a winning playbook and be a value-based CFO versus a cost-cutting CFO.

21:38 - The start of Guild Garage Group

24:14 - Start with relationships first, take extra time.

25:05 - How to apply the experience into an Action Plan

28:35 - The 5 Pillars of Leadership Relations

30:30 - Brianna Skington, the best example of a relationship built from Trust, Creativity and amazing solutions in Marketing.

33:38 - prioritize personal check-in first in one-on-one meetings is called the "oxygen goal" 35:34 - The best influencers are those who are very easily influenced and allow themselves to take in different perspectives.

38:30 - "People don't care how much you know until they know how much you care,"

42:39 - The Guild Garage Group has a leadership development course that teaches the five characteristics: trust, listening, respect, influence, and care.

46:58 - The importance of protecting your time

52:56 - The ONE Thing by Gary Keller– discusses that saying "yes" to something is saying "no" to everything else, putting time into perspective.

55:19 - The makers versus managers concept

1:12:10 - How to build a Strong Culture focusing on the positive

1:21:30 - Get the right systems in front of your Team

1:29:05 - The Ability to build constructive criticism

1:36:20 - What is your Goal?

1:47:25 - The Voice inside your Head talks to you than any other Voice

1:54:50 - Episode Ends

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In this episode, we are joined by a familiar face and longtime friend, Zac Garside. His professional journey started at Power Selling Pros, where he helped home services businesses to improve their CSRs performance and the call center experience.

Since we last spoke, Zac had his email marketing business get acquired by Prolific Brand Design, a powerful brand design company in the trades that has retained Zac as their CEO! He has still maintained his expertise in Email Marketing adding it to the unique suite of services that Prolific offers, Why? Because no matter what new shiny platform or new tactic emerges, email marketing simply refuses to die. For eight and nine-figure businesses, the secret to sustained profit is almost always hidden within their existing email list.

If you feel like you’re sitting on a goldmine of customer data but don't know how to tap into it, this episode is for you. Zac breaks down the exact framework for turning a quiet list into a consistent source of booked calls.

Connect with Zac Garside:

Website: https://prolificbranddesign.com/

LinkedIn: https://www.linkedin.com/in/zacgarside

Instagram: @zacgarside

Free Resource: Download Zac’s E-book, How to Sell Premium Services with Email

Time Stamps:

00:10 - Profit for eight or nine-figure businesses often comes from their email list.

00:23 - Introduction of guest Zac Garside

00:41 - Zac started his own company

01:52 - How Zac Garside got into email marketing.

06:01 - The importance of internships and acquiring specific skills

10:31 - The customer lists that aren't being used and promises immediate business

11:09 - The importance of remembering "you are not your customer" and overcoming the fear of overwhelming people with emails

12:33 - Zach Garside lists several free and paid ways to grow an email list

16:44 - Email is unique in that it doesn't cost more to publish many emails

17:50 - The from line is more important than the subject line

21:30 - A simple method for activating an earned customer database

22:12 - Zach Garside uses a "wake up campaign" email three times a week.

25:07 - How to stand out and cut through inbox clutter and how to get emails to the main inbox instead of the promotions tab.

27:56 - Example of a plumbing email for Thanksgiving using uniques “from” and “Subject” lines

29:12 - "Entertainment beats education”

34:41 - The key to stand out is to be unpredictable

35:53 - Example of an HVAC company switching up emails by using the different personalities of two founders

44:03 - The importance of knowing your customer

46:30 - Zach Garside offers a freebie on his website: https://zacgarside.berserkermail.com/[free_book]_how_to_sell_premium_services_with_email 47:04 - Contractors are "literally sitting on a gold mine" with their email lists

48:19 - Post-show insight: sometimes the win in email marketing is just sending the email instead of being bogged down trying to craft the perfect one.

50:10 - Show ends.

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After 250 episodes of HVAC Success Secrets Revealed and parting ways with my business partner, I thought I’d be back behind the mic in a week. But, Life had other plans. I stepped into a new role as a Fractional CMO with Free Agency and became a dad. Now, after a full year of learning, growing, and observing from the sidelines, I’m finally ready. Welcome to the official launch of Let’s Vent Podcast!. On this show, I’m giving HVAC Contractors, Plumbers, Electricians, and Business Owners the time to get on the soapbox.
We’re venting about the messy stuff, the real world mistakes, the shifting regulations, the AI new era, and the headaches of inflation and labor shortages.
I’m Evan Hoffman, and I’m ready to vent. Are you?