Jennifer Steward has spent the last decade doing something most real estate investors avoid entirely: personally cold calling off-market property owners, thousands of hours of it, until she'd built a repeatable system worth teaching. Today, she runs Phone Phoenix Agency, leading a team of more than 200 trained virtual assistants who handle cold calling, lead management, and appointment setting for investors and agents across the country, and is backed by more than 155 five-star reviews. In this conversation with Jason Seward, Jennifer gets specific about what actually works in 2026: why listening for silence matters more than any script, why cold calling is real, unglamorous labor and not a passive income source, and the honest math behind what it costs and how long it takes to get your first deal. She also opens up about the poverty she grew up in and why she believes real resilience, not talent, is what separates the operators who make it from the 95% who don't. If you've been burning through marketing budget without a real system behind it, this episode is a grounded, no-fluff look at what it actually takes. What You'll Learn in This Episode How to listen for silence on a sales call instead of filling every gap, and why that single habit changes your close rate Why cold calling is real, labor-intensive work rather than a passive income source, and what that means for your expectations What it actually costs and how long it takes to get your first deal, from $4,000 to $7,000 per deal and three to four months of spending before any income comes in Why "specificity of motive" is the real signal a seller is ready to sell, no matter what price they name How to structure a virtual assistant team, from a $540 a month starter package to a full-time hire, and what results to expect at each level Why making offers, not perfecting your comps, is the actual bottleneck holding most investors back from their first deal Timeline Highlights [0:16] – Introducing Jennifer Steward, founder of Phone Phoenix Agency and a 200+ person cold calling and lead management team [2:37] – Jennifer's connection to Jim Ingersoll and Dealmaker, starting with a client named Lloyd on Upwork [4:47] – Speaking at a Dealmaker event and watching her income and net worth grow six figures every time [9:19] – Jennifer's path from cold caller to lead manager to quitting her W-2 job in April 2021 [13:38] – What most investors misunderstand about people: it's what they don't say, not what they say [14:30] – The psychology of silence, and how the brain rewires around listening the way a blind person's does [16:22] – The real numbers: one lead per eight-hour shift now versus five per hour before Covid [17:14] – Why BatchDialer's reputation management feature is critical to actually reaching people [19:36] – Why Jennifer stopped offering texting services after carrier shutdowns in August 2023 [22:09] – The sales mentor who taught Jennifer to shut up and let silence do the work [28:42] – Why quality of leads has gone up even as quantity has gone down since Covid [30:54] – Jennifer's own story of childhood poverty and why she believes it built her resilience [34:48] – Why military veterans tend to be her most durable clients [36:22] – When an investor should hire their first virtual assistant instead of cold calling themselves [38:06] – The real cost of a deal: $4,000 to $7,000 depending on market, and 3 to 4 months before your first close [43:43] – Why "specificity of motive" matters more than the price a seller names [48:14] – What working with Phone Phoenix Agency actually looks like, from a $540 starter package to full-time [54:23] – Why making offers, not perfecting your numbers, is what actually gets deals done [59:37] – Jennifer's philosophy on legacy, and the mentor who taught her the abundance mindset [1:03:27] – Closing thoughts and how to reach Jennifer directly Resources Mentioned Phone Phoenix Agency — Jennifer's lead generation and virtual assistant company for real estate investors, wholesalers, and agents Jennifer Steward — contact by email at jen@rtidatasource.net BatchDialer — the dialer Jennifer's team uses, credited for its reputation management and number replacement features — https://batchdialer.com Rehab Valuator — the comps and deal analysis software created by Daniil Kleyman, which Jennifer has used for seven years — https://rehabvaluator.com X Leads CRM — referenced as a CRM that can automate offer sending; exact product name and URL could not be independently confirmed 608B Capital — episode sponsor, a hard money lender for fix and flip, BRRRR, and value add deals, plus a debt fund for accredited investors — https://608bcapital.com Elite Dealmakers Discount Program — episode sponsor, nationwide discounts at Lowe's, Sherwin Williams, and more for community members — https://elitedealmakers.com/discount Connect and Subscribe If there's one thing to take from this episode, it's Jennifer's line that the business you're in is the business of making offers. Go count how many offers you actually sent this month, and if the answer is zero, that's the fix before anything else. Share this episode with someone who keeps saying the leads aren't converting, and go check out Phone Phoenix Agency if you want a team like Jennifer's in your corner. Subscribe, leave a review, and pass it along to someone serious about leveling up. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.
