Acquiring Minds: "$60m Roll-Up That Started With an SBA Acquisition"

Host: Will Smith
Guests: Onu Okba & Brian Boland, HTL Freight
Date: October 2, 2025

Episode Overview

This episode uncovers the story of Onu Okba and Brian Boland, founders of HTL Freight, who built a $60 million revenue logistics platform through a roll-up strategy that started with a small SBA-financed acquisition. The conversation dives deep into how they identified their niche, bootstrapped growth through careful working capital management, made key strategic acquisitions, and eventually raised outside capital—with lessons for would-be acquisition entrepreneurs.

Key Discussion Points & Insights

1. Origins: Two Paths Converge on Entrepreneurship

• Onu Okba's Journey (06:24)

  • Came from Lagos, Nigeria to the US seeking opportunity.
  • Early exposure to entrepreneurship via his family and work as an accountant.
  • Pivoted to logistics after a friend's uncle was laid off as a truck driver; saw the need/opportunity and started a business in logistics.
  • After selling his first business and gaining PE exposure, realized the real economic upside was in operating/owning, not just advising or financing deals.
  • Met Brian Boland at business school (Goizueta, Emory); both took an "Entrepreneurship through Acquisition" class and decided to partner up.

• Brian Boland’s Background (15:12)

  • Originally from Ireland; family of entrepreneurs.
  • KPMG consultant, then worked in M&A for a large building supply firm, CRH.
  • Emigrated to Atlanta, did his MBA at Emory.
  • The ETA class sparked the realization that buying businesses could derisk entrepreneurship: “You can flip the 90% risk of failing as a startup and flip it into 90% success if you just manage the free cash flow appropriately.” (16:35)

2. Deal Sourcing and Strategy Formation

• They searched for 2.5 years, COVID hit mid-search, leading to a more focused, micro-niche thesis.
• Originally considered all areas—warehousing, asset-based trucking, 3PLs—eventually honed in on non-asset freight brokerage due to:
  • Fragmentation & scalable roll-up potential.
  • Fit with their backgrounds in logistics from both the carrier and customer side.
• “As time went on, we found it more beneficial to focus in a specific niche… non asset third parties.” – Onu Okba (20:47)

3. The First Deal: Small Platform, Big Vision

• Used personal assets and an SBA loan for the first acquisition (about $1.5M deal, $500k SDE, $4.5-5M revenue). (29:02, 79:17)
• Retained 100% ownership by not raising outside capital until the fourth acquisition.
• Location in Charlotte, NC was important—geographic proximity mattered operationally even if it wasn’t “close” to Atlanta.
• The business was operationally archaic but had “hair” (opportunities to upgrade & add value), especially through process digitization and working capital improvements. (34:59)
  • “Literally were still using pen and paper for everything… we turned that from 30-40 minutes to 30 seconds.” – Onu (35:56)

4. Unlocking Cash: Working Capital Optimization

• Working capital management was the “x-factor”—by optimizing receivables and payables and leveraging vendor dynamics, they quickly increased available cash to fuel further deals.
• “Working capital execution is, like, hand-to-hand combat… so many people go into deals not understanding it.” – Brian (37:06)
• Leveraged an SBA Express line of credit for liquidity.
• This careful management allowed them to do a second deal within nine months without outside equity—using business-generated cash flow and a seller note. (53:33)

5. Thesis Evolution & Building a Full-Service Platform

• Initial goal: Dominate the flatbed brokerage niche.
• Quickly realized greater opportunity—and easier acquisitions—by expanding into complementary niches (hazmat, LTL, refrigerated, etc.) via targeted bolt-ons. (26:04)
• Geographic diversity was also important; acquisitions spread across the US.

6. Bootstrapping vs. Raising Money

• Held off on external equity until deal four; allowed them to negotiate on better terms and avoid early, expensive dilution.
• “What we raised eventually after three deals was probably close to 10 times what we could have raised at the start for the same equity dilution.” – Brian (31:19)
• When they did raise (~$3M for deal #4), they mostly used their professional network and alumni connections for “smart money” (board members with industry experience) rather than traditional search fund investors. (68:45)

7. Culture, Leadership, & Personal Growth

• Both founders credit their athletic backgrounds with building the stamina and discipline needed for rapid deal execution and operational turnaround. (56:16)

• Emphasized the importance of getting comfortable with being bad at new things to enable eventual mastery.

  • “In order to be good at anything, you have to be bad first… For me, it’s putting myself in situations that I may not be the best at. But just getting those reps… being comfortable being bad and not letting being bad stop you from moving forward.” – Onu (64:35)

• Found unexpected fulfillment in developing employees and watching internal growth across their portfolio. (59:25)

8. Deeper Dive: How Freight Brokerage Works (40:38)

• HTL acts as an intermediary between manufacturers/distributors and a fragmented network of “mom-and-pop” carriers.
• Takes a spread between what the customer pays and what they pay the carrier.
• Adding managed services (consulting, tech integration, supply chain optimization) as a value-add offering—makes up about 20% of revenue; the rest is core freight brokerage. (43:59)

9. Key Takeaways on Building a Roll-Up

• Importance of finding the right first deal—not necessarily a big one, but one with operational or working capital “juice.”
• Pacing is demanding—partnership and complementary skill sets (finance/ops, dealmaking/operations) are essential for rapid growth.
• “Don’t go into it [a partnership] just with a buddy… Find somebody that complements your skill set.” – Onu (87:04)
• Roll-ups require constant evolution of the thesis and openness to pivot as industry realities present themselves.
• Culture fit and employee “excellence” becomes more important at scale.
• “Hard times make strong people.” – Brian (84:20)

Notable Quotes & Memorable Moments

• “You can flip the 90% risk of failing as a startup… into 90% success if you just manage the free cash flow appropriately.”
  — Brian Boland (16:35)

• “Working capital execution is, like, hand-to-hand combat… There’s no classes on working capital in school… It’s probably one of the single most important dynamics of small business.”
  — Brian Boland (37:06)

• “What we raised eventually after three deals was probably close to 10 times what we could have raised at the start for the same equity dilution.”
  — Brian Boland (31:19)

• “In order to be good at anything, you have to be bad first… being comfortable being bad and not letting being bad stop you from moving forward.”
  — Onu Okba (64:35)

• “We wanted to come out, get a track record and prove the thesis… If it didn’t work out, we were on the hook. We didn’t want a situation where it didn’t work out and we had investor capital on the hook as well.”
  — Onu Okba (33:06)

• “We were eating, breathing the business… We’re moving at a very, very fast pace. The biggest challenge was bringing people along on the trajectory that you are going.”
  — Onu Okba (57:32)

Important Segment Timestamps

| Timestamp | Segment Description | |------------|-------------------------------------------------------------------------------------------| | 06:24 | Onu's background: immigration, career path, and entrepreneurial inspiration | | 15:12 | Brian’s introduction—Irish upbringing, finance in big industry, the ETA “aha” | | 20:47 | Search process: how the focus on logistics niches evolved over time | | 29:02 | First acquisition details: deal size, financing, why they bootstrapped | | 34:59 | What made their first deal attractive: location, “hair,” working capital opportunity | | 37:06 | Deep dive on working capital management as a driver of acquisition velocity | | 40:38 | How a freight brokerage works: dollar flows, service lines | | 53:33 | How they used early cash flow and working capital to finance the next acquisition | | 56:16 | How their backgrounds & culture (athletics) informed the company’s speed and execution | | 68:45 | Their approach to raising external capital for bigger deals: terms, networks, and lessons | | 64:35 | Onu’s philosophy about getting good at something by being willing to start out “bad” | | 79:17 | Current numbers: employees (~70), platform revenue, growth since first acquisition | | 84:20 | Would they recommend this roll-up approach to others? Hard-won lessons and key conditions |

Conclusion

Onu Okba and Brian Boland’s journey with HTL Freight illustrates a powerful example of acquisition entrepreneurship. They started with a modest, “hairy” business, bootstrapped and optimized it, and parlayed those skills into rapid, niche-focused roll-up growth—eventually raising outside capital on their terms. Their advice to future searchers: find the right first deal (value-add potential matters more than size), surround yourself with complementary talent, expect to stretch personally and professionally, and put in the “reps.” Their story is a compelling case study for anyone considering a big-building, hands-on approach to acquisition entrepreneurship.