Sean Connolly
Sean Connolly has been a guest on Collecting Keys, the real estate investing podcast hosted by Mike DeHaan, Dan Austin and Dylan Koch.
Scaling a $50 Million Flipping Business While Working 1-Hour Days w/ Sean Connolly
Sean Connolly, a Chicago investor running a roughly $50 million flipping and holding business, explains how documented systems, meeting cadences, and virtual assistants let him spend about an hour a day in that company. He walks through his auction-buying process (VAs filtering foreclosure lists, door knockers verifying condition, fixed 20% margin strike prices), why he pivoted into direct-to-seller acquisitions as auction margins vanished, and how he builds online lead gen, follow-up, and KPIs through his staffing and systems company Scale Virtually.
Key takeaways
- Auction buying can be systematized by setting a fixed margin (Sean uses 20%) as the strike price so VAs and drivers can produce MAOs without the owner; VAs narrow 1,000+ monthly Chicago foreclosures to a top 100 that two drivers inspect.
- Auction margins in Chicago collapsed — Sean went from closing about 2 of 10 bids to 1 of 25 — which pushed him to buy a direct-to-seller company; he now sees higher margins and avoids court and eviction timelines.
- Simpler, faster flips beat heavy gut rehabs: switching from two- to six-flat full renovations to simple deals roughly doubles profit through velocity of capital, even at lower per-deal margin.
- The first hire for any operator should be an executive assistant, but only after documenting how you want the work done — Sean says the documentation is 95% of the battle, and SOPs only stick when tied to KPIs and recurring meeting cadences.