8 Real Estate Deals in 2 Years While Working Full-Time (Raising 4 Kids)

Summary of 8 Real Estate Deals in 2 Years While Working Full-Time (Raising 4 Kids)

by BiggerPockets

46m•March 23, 2026
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Overview of 8 Real Estate Deals in 2 Years While Working Full-Time (Raising 4 Kids)

This episode of the Real Estate Rookie (BiggerPockets) features Molly Shepard — Army veteran, full‑time W-2 employee at a top VA lender, foster mom and mother of four — who, with her husband Kyle, closed eight flips and acquired two rentals in 22 months while balancing family and full‑time work. Molly explains how they sourced deals, funded projects, scaled volume, learned from mistakes, used tech (AI) to improve processes, and created seller‑help niches (estates/assisted living). The episode is practical, mindset‑forward, and packed with replicable tactics for novice investors.

Guest background

  • Molly Shepard: Army veteran; works full‑time training loan officers at the nation’s top VA lender; mother of four (including a foster daughter).
  • Kyle (husband): Initially W‑2, transitioned to full‑time investor during their push to scale flips.
  • Result: 8 flips, 2 rentals in ~22 months; significant deal activity and systems built while maintaining family life.

Key highlights & metrics

  • First flip: Purchased $115K, rehab ~$35K, listed $195K, sold for $200K. Rehab scope focused on market‑appropriate updates, not personal tastes.
  • Funding for that first deal: Hard‑money lender covered purchase & rehab; the couple only paid monthly interest/points (no initial cash outlay on that deal).
  • Volume snapshot (90 days): Kyle walked 114 properties, made 47 offers, bought 5.
  • One losing deal due to missed due diligence: ~$9,000 termite damage from water pooling at foundation (no gutters).
  • Sourcing mix: on‑market listings, realtor relationships (Friday walkthroughs), referrals, estate/probate leads, assisted living/memory care outreach.

Notable quotes

  • “Just go do the thing — pull the trigger and figure it out.”
  • “What’s the worst that can happen?” (Used to get family / partners comfortable with risk.)
  • “Numbers don’t lie” — Molly shows her underwriting to agents/sellers to justify low offers.

Deals & stories (notable examples)

First flip (the granny house)

  • Condition: 50‑year old home full of dated finishes and decades of belongings; clean but outdated.
  • Strategy: Market‑appropriate cosmetic rehab (flooring, paint, cabinets) rather than overbuilding for the buyer profile.
  • Numbers: Buy $115K + $35K rehab → sold for $200K.

Fourth flip (most meaningful)

  • Bought from a family connected to their kids’ daycare; after rehab the buyer was the former owner’s daughter — kept the home in the family. This was an emotional win and demonstrates the positive community impact of thoughtful flipping.

Systems, tools & tactics they used

  • Time management: Listen to podcasts/educational content during walks and downtime; work numbers at kid events; trade small blocks of time for productive work.
  • Deal sourcing:
    • Regular Friday realtor walkthroughs (10–12 properties) to see many homes quickly.
    • Social media “we buy houses” posts (Facebook/Instagram stories; now TikTok).
    • Direct outreach to estates, probate, assisted living, and memory care directors — provide a packet/postcard offering to take the burden off grieving families.
    • Realtor relationships: 3–4 trusted agents who bring on‑ or off‑market opportunities.
  • Offers & negotiation:
    • Make offers below asking price; show your numbers to justify offers.
    • Accept that many offers will be rejected at first; sellers may return later.
  • Funding:
    • Started with hard money that covered purchase + rehab; later added private money for faster closings.
  • Process controls:
    • Standardized walk‑through forms/checklists used on every property to prevent missed items.
    • Every property is videoed; husband personally views each property.
  • Tech / AI:
    • Use AI to analyze photos/videos for issues (e.g., HVAC model/warranty problems, count outlets, spot missing features).
    • AI used as an extra set of eyes to catch items humans might miss and speed estimating.

Mistakes & lessons learned

  • Big miss: Skipping inspections on a wholesale flip; lack of gutters caused foundation exposure → termite damage (~$9K). Result: lost money on that flip.
  • Root causes: Overload from running multiple projects, trusting others’ eyes, and relaxed checks/balances while scaling.
  • Process fixes:
    • Reinstate strict inspection and walkthrough protocols.
    • Video every property and apply AI / consistent forms.
    • Ensure one partner personally views each asset.

Mindset & buy‑in (family & fear)

  • Overcoming analysis paralysis: Routine consumption of content guided them to “just do it”; repeated exposure to similar advice helped cross the action threshold.
  • Handling imposter syndrome: Put helpful offers and public posts out there despite feeling like a fake; focus on solving sellers’ burdens rather than pretending to be experts.
  • Getting spouse/family on board: Use concrete conversations (what’s the worst case?) and present the plan; show that failure can still lead to a return to W‑2 employment.
  • Dealing with sellers/agents: Be transparent and show underwriting when necessary — “numbers don’t lie.”

Actionable checklist for rookies (what to implement today)

  1. Block small, consistent time (early morning or kid practice) for learning and underwriting.
  2. Attend weekly realtor walkthroughs or investor open houses to see volume and learn what others look for.
  3. Post simple “We buy houses” messages on social stories and create a clean 5×7 postcard/business card for assisted living/estate outreach.
  4. Standardize a single walkthrough checklist and record every property on video.
  5. Use AI tools to scan images/video for red flags (HVAC models, structural clues, missing gutters, outlet counts).
  6. Always run comps and decide rehab scope by buyer profile (don’t renovate for yourself).
  7. Make offers below asking — be ready to show your numbers to justify them.
  8. Build relationships with a few reliable realtors and lenders who understand novice-friendly financing.
  9. Have an inspection policy — don’t skip due diligence even on wholesale/off‑market deals.
  10. Start small, accept mistakes, and scale process improvements quickly.

Resources & contact

  • Molly Shepard: Facebook — Molly Shepard; TikTok — Real Estate Molly; Instagram — real_estate_molly.
  • Sponsors mentioned/education resources in episode: BiggerPockets/BAM, Shopify, Indeed, Cost Segregation Guys, Host Financial (sponsors from the episode).

This episode is particularly useful for rookies who need practical ways to balance family/work with real estate, those wanting reproducible sourcing strategies (on‑market + realtor walk‑throughs + assisted living outreach), and anyone who needs a simple framework to overcome analysis paralysis and begin making offers.