A Bullpen Company
Obsidian Group launched in 2018 as an investment-focused CRE brokerage, primarily investing in its own deals. Not formally trained in commercial real estate, Daniel learned underwriting and deal execution through mentors, friends, and whatever information was publicly available. His technical capability grew as the business scaled.
However, as Obsidian kept buying properties, the demands of capital partners rose:
Daniel tried to keep stretching Excel, but the gap between what was “possible” and what was “expected” widened.
A key inflection point came during a shopping center acquisition:
The deal was a success, but it exposed operational limits. Obsidian’s underwriting process was reaching a breaking point.
An analyst working with Obsidian made the call plainly:
“I’ve pushed Excel to the max of what it’s capable of doing.”
That was the moment the requirement became clear: Obsidian needed to move to a more robust tool, ARGUS, to underwrite new deals.
Daniel tried to leverage his current team first. He had a teammate (a chemical engineer) attempt to learn ARGUS through available online tools.
The engineer tapped out.
If a chemical engineer couldn’t brute-force it, Daniel knew the odds of self-teaching ARGUS while running the business were slim.
Obsidian needed real expertise, without the full-time commitment.
Obsidian didn’t have W-2 employees, and hiring a full-time analyst would have forced them into infrastructure they intentionally avoided:
Daniel also pointed to market realities:
A fractional analyst gave Obsidian a clean solution: access the skillset, pay for the output, avoid the org build.
Daniel engaged OnDeck and quickly received multiple analyst candidates. OnDeck’s process did two things:
As Daniel described it, even when an analyst wasn’t a fit, the model created momentum:
“... you interview multiple people, choose one, and if it’s not working, you can transition quickly”
Obsidian started receiving solid deliverables quickly, and the value proposition became obvious:
“Why would we ever go anywhere else? The cost-benefit analysis was such a no brainer.”
Fractional analyst support wasn’t a compromise, it was a better way to operate.
Over time, Obsidian’s initial analyst relationship became less reliable due to personal life issues outside of OnDeck’s control.
This is usually where vendor relationships fracture.
Instead, OnDeck’s response strengthened trust:
Daniel’s takeaway was direct:
“I truly mean that… you made our issue a priority. I felt really respected.”
Obsidian has now worked with their current analyst, Ian, for multiple years. The dynamic is clear and scalable:
Daniel emphasized three things that mattered most:
“Ian’s attention to detail and lack of errors is pretty remarkable.”
Daniel was candid on ROI:
“I feel like I’m getting more than the value of what I’m paying for.”
Most of the analysts on OnDeck would earn $200K+ in a traditional job, but the fractional model allows you to validate fit and get immediate output without the downsides of traditional hiring.
He also emphasized a key structural advantage:
“Even if the first person isn’t perfect, you’re not starting from scratch - you can shift to a better fit. It truly is a no risk proposition.”
Obsidian didn’t just get ARGUS support. They validated a way to scale expertise, without scaling headcount.
“OnDeck works as intended every time. If there’s conflict, it’s resolved immediately.”
“OnDeck works as intended every time. If there’s conflict, it’s resolved immediately ... Why would we ever go anywhere else? The cost-benefit analysis was such a no brainer.”
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