How Tailor Hartman Built and Scaled an Accounting Firm
Podcast
If you are searching for how to grow an accounting firm, Tailor Hartman’s story offers a practical blueprint. He went from a $25/hour side gig on Upwork to leading a firm approaching seven figures. His approach combines authenticity, steady growth, and building a niche within the accounting community.
Key takeaways
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Start where buyers already are. Tailor Hartman built his first $200,000 year almost entirely on Upwork, landing cleanup projects that turned into recurring retainers.
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Price low to win early trust, then step up. He began with a $25/hour side gig, proved value, and moved qualified clients to ~$2,000/month retainers.
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Make authenticity your edge. Handwritten proposals, quick research on each prospect, and a human tone drove a ~90% close rate once a call was booked.
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Niche by platform to unlock referrals. Becoming “the NetSuite guy” among peers turned conferences and community into a steady two-clients-per-month pipeline.
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Use AI as an augmenter, not a replacement. Focus on tools that surface anomalies and talking points so fixed-fee work delivers more value without more hours.
Who is Tailor Hartman and what did he build?
Tailor Hartman is the founder of Celerity Accounting, a firm that serves QuickBooks Online and NetSuite clients from bookkeeping through CFO-level services (plus payroll, AP, and adjacent work). In three years, the firm progressed from a solo practice to a team (his first contractor later became his first full-time hire) and reached the following run-rate:
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Year 1 revenue: $200,000
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Year 2 revenue: $350,000
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Year 3 revenue: $550,000
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Current run-rate: ~$60,000 MRR (about $720,000 ARR), adding two clients per month
“In year one… $200,000. Year two $350,000. Year three $550,000… We are over $60,000 a month right now.”
The journey began while Tailor was still employed: he opened an Upwork account, took a $25/hr cleanup gig, “crushed it,” collected reviews, and stacked better clients. By the time he resigned, he had ~$6,000/month in booked work and needed ~10 hours a week to deliver it.
“I priced it really low… I hand-wrote every one of those proposals… And by the time I quit, I had about $6,000 a month lined up on Upwork.”
How did he land his first clients?
Tailor started while still working full-time, using Upwork as his launchpad.
“It must have been 25 bucks an hour, which is way too cheap, right? But I crushed it, got another gig, crushed it, crushed it. Then you start to get reviews… By the time I quit my job, I had about 6,000 a month lined up on Upwork.”
Within three months, he had recurring side income of $6,000 per month, which gave him the confidence to resign and go full-time.
He emphasized two things that worked early:
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Pricing low to win first gigs. His first projects were only $25/hour.
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Handwritten, authentic proposals.
“I hand wrote every one of those proposals… A lot of people just copy and paste and do it a thousand times a day. But I was very authentic with it.”
Practical Example: Winning Early Clients on Upwork
For accountants starting on marketplaces like Upwork or Fiverr:
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Target urgent problems (cleanup, bank recs, overdue books).
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Write personalized bids (reference location, website, or products).
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Leverage reviews. Early testimonials compound credibility fast.
How did he turn cleanup gigs into recurring clients?
Tailor’s strategy was simple: deliver great cleanup work, then offer ongoing monthly accounting.
“I’d crush it on the books and then they would basically ask me to stay on and do their monthly accounting… I think the only app I had was Ignition back then and I would just throw out a number.”
One client generating $25 million in revenue agreed to pay about $2,000/month after he cleaned their books.
This became his early formula:
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Cleanup → Win trust
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Transition → Monthly close and reporting retainer
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Price → Around $2,000/month for established QBO clients
To make that transition seamless, firms can systematize their monthly close with Jetpack Workflow’s platform.
Applying Tailor’s Process: Cleanup → Retainer
A repeatable process firms can use today:
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Offer fixed-fee cleanups to solve urgent issues (bank recs, accruals, AR/AP).
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Present a before-and-after report to prove value.
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Transition to monthly recurring services with clear deliverables.
What made his proposals different?
Tailor relied on authenticity rather than templates.
“I found their company online. I saw they were in Chicago. This was a shoe company in Chicago. And I’m like, ‘Hey, I’m in Madison, which is like two hours away from you. I’m a real person. I have my CPA. I saw your company. You sell this kind of shoe. That’s super cool.’ I was just trying to relate with them and give them a reason to trust me faster.”
This extra effort drove results:
“Once you get them on that call, my close rate was like 90 percent.”
Modern firms can boost close rates even further by using Jetpack Workflow to standardize proposals, automate engagement letters, and streamline client onboarding.
When did he hire his first team member?
By the end of year one, Tailor hired his first contractor through Upwork.
“I tested her out for maybe three or four months, and trained her on the way that I like to do things and my quality standards. She didn’t have an accounting degree… she just kept crushing it… I need to hire her full-time.”
They learned together:
“Prepaids, accruals, AP workflows… We broke Bill.com together on a client that has 350,000 SKUs.”
This hire later became his first full-time employee and is still with the firm more than two years later.
How did he move beyond Upwork?
By year two, Tailor realized Upwork was no longer worth the effort.
“I was probably making 25,000 a month at that time when I decided it’s not worth my time to keep going on here and applying.”
Instead, referrals became the primary growth channel.
“I’m the NetSuite guy to other accountants a lot of the time, and that has been really lucrative for me.”
Example Application: Referral Growth for Accounting Firms
To build referrals in accounting:
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Pick a niche (platform like NetSuite or an industry like SaaS).
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Help peers when they encounter your niche.
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Stay visible at conferences and on LinkedIn/X.
What role did conferences and community play?
Attending events pushed him out of his comfort zone but paid off.
“I went to Intuit as my first conference in the first year of starting my business… This one breakfast was worth it for me to come all the way to Vegas and meet really inspiring people.”
He joined Future Firm, which gave him structure and helped him meet key influencers in the accounting space. These community connections turned into steady referrals.
How does he view AI in accounting?
Tailor is cautious about “AI-washed” features but sees real promise in augmentation.
“Adding chat bots to your software that only work when you say five different things, that’s not adding AI to your software really. So, I think there’s a lot of overhyping.”
He believes AI should help accountants deliver more value without adding hours.
“Point out weird things like your rent went up 500 dollars… Or like hey we see that this interest is trending up but the rest of the industry is trending down.”
How Accounting Firms Can Apply AI Today
Practical AI use cases in firms today:
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Detect unusual vendor payments or expense spikes
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Draft monthly client updates for review
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Benchmark clients against industry peers
Conclusion
Tailor Hartman’s story is a practical blueprint for how to grow an accounting firm:
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Start with marketplaces like Upwork to land cleanup gigs.
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Turn projects into $2,000/month retainers.
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Be authentic in proposals.
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Build referrals around a niche (like NetSuite).
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Leverage community and selective AI tools to scale efficiently.
By combining authenticity, consistency, and repeatable workflows, firms can grow from solo practice to seven figures.
FAQS
1. How did Tailor Hartman get his first accounting clients?
He used Upwork to land cleanup projects at $25/hour, delivered strong results, and converted those into $2,000/month recurring retainers.
2. What was Celerity Accounting’s revenue growth?
Year 1: $200k. Year 2: $350k. Year 3: $550k. Current run rate is about $60k/month recurring (~$720k ARR).
3. Why did Tailor Hartman become known as the “NetSuite guy”?
He self-taught NetSuite for a client, gained expertise, and peers began referring him whenever they had NetSuite leads.
4. Does Tailor think AI will replace accountants?
No. He believes AI should augment accountants by surfacing anomalies and improving client communication, not replace them.
Learn From Tailor Hartman’s Growth Playbook
From $25/hr Upwork gigs to $720k ARR, Tailor Hartman scaled Celerity Accounting by systematizing delivery and focusing on referrals. See how workflow automation supports that same growth path.
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