In this episode, Jay and I continue the Kickstarter series by helping you bridge the gap between big, long-term vision and what you can actually start doing right now. We talk honestly about time, priorities, and why waiting for the “perfect season” is usually the thing holding people back.

This conversation is packed with real-life examples—from lifestyle goals like travel and freedom, to real estate strategies, health goals, and cash-flow planning. We walk through how to create waypoints that allow you to test your vision before going all in, so progress feels achievable instead of overwhelming.

Episode Timeline:

[0:01] – Why time is the most valuable asset we have

[0:42] – Breaking down big vision into doable pieces

[1:59] – Planning life first, then fitting business into it

[3:07] – Rethinking ownership: boats, rentals, and access vs. assets

[5:27] – Why convenience and time often matter more than status

[6:39] – Designing your lifestyle instead of defaulting to hustle

[8:02] – Using waypoints to test a vision before committing fully

[8:41] – The Florida example: easing into a major life change

[9:23] – Health, fitness, and setting realistic, measurable goals

[11:04] – Cash-flow conversations and building income without burnout

[12:50] – Turning weekly habits into long-term results

[14:54] – Short-term rentals, hospitals, and intentional acquisition strategies

[16:13] – Setting small, achievable targets that compound over time

[18:05] – Why clarity beats comparison every time

[20:07] – Aligning income goals with the lifestyle you actually want

[21:47] – Stacking habits and protecting quality time

[24:00] – Putting the vision on the calendar so it actually happens

[25:21] – Final encouragement: progress over perfection

5 Key Takeaways:

1. Time is the ultimate currency—build your business to protect it.

2. You don’t need to go all in to move forward; start with waypoints.

3. Access can replace ownership when lifestyle is the real goal.

4. Big visions become achievable when broken into daily actions.

5. Your calendar should reflect your values, not just your to-do list.

Links & Resources:

• Join our free Facebook group for real estate and lifestyle conversations: [Insert link]

• Vision templates and exercises shared during the Kickstarter series

• Learn more about working with us at: JayAndAnnieAdkins.com

If this episode helped you rethink how you approach your goals, please rate, review, and follow The Real Estate Ride. And share it with someone who needs permission to start living their vision now—not someday.

In this episode, I sit down with real estate investor and coach Stephanie O’Brien to unpack her journey from getting licensed in 2006 to becoming a powerhouse in short sales, investing, and now coaching others through major transitions. Stephanie shares how the 2008 crash shaped her career, why she chose to specialize in solving tough problems, and how that path eventually led to her own personal and professional reinvention.

We dive deep into the mindset shifts required to go from chaos to clarity, how to recognize when you’re out of alignment, and why letting go of what no longer serves you is often the key to leveling up. If you’re feeling stuck or stretched thin, this conversation will help you realign and reset with purpose.

Episode Timeline:

[0:00] – Intro: how Stephanie got started in real estate pre-2008 crash

[1:02] – Why she leaned into short sales instead of running from the chaos

[2:21] – Building a business focused on helping people through hard transitions

[3:45] – The power of coaching and clarity during seasons of confusion

[5:17] – How to know when your goals are no longer in alignment

[6:29] – Breaking free from the “more is better” mentality

[7:38] – Getting honest about burnout and redirection

[8:50] – Stephanie’s own reinvention journey and what sparked it

[10:04] – From transactional real estate to transformational coaching

[11:16] – Creating margin in your life and business

[12:25] – Why entrepreneurship often reveals what we’ve ignored

[13:48] – Setting new standards and boundaries after burnout

[15:12] – Stephanie’s current coaching work and what lights her up

[16:03] – What alignment looks like—and how to find it again

[17:36] – Final words of encouragement for anyone stuck in the grind

5 Key Takeaways:

1. Realignment often starts with being honest about what’s not working.

2. Short sales and creative investing solve real problems for real people.

3. Burnout is a signpost—not a failure.

4. Your next level may require releasing what worked in a past season.

5. Coaching and community can create clarity faster than going it alone.

Links & Resources:

• Connect with Stephanie on Instagram: @the.real.stephanieobrien

• Coaching or speaking inquiries: Stephanie’s Website

• Join our free Facebook group for real estate investors: [Insert link]

• Learn more at JayAndAnnieAdkins.com

If this episode gave you the clarity or courage to pivot, rate and review The Real Estate Ride. And don’t forget to share it with someone who needs to hear they’re allowed to evolve.

In this episode, Jay and I break down exactly who’s on our real estate investment dream team—and why having the right people in the right seats has been key to scaling our business. From contractors and lenders to attorneys and agents, we walk through every role we rely on to flip, buy, rehab, and manage rentals efficiently.

We also talk through how we vet team members, how we use personality assessments to match people to the right jobs, and why you don’t need to do everything (or hire full-time) to build momentum. Whether you’re just starting or ready to scale, this episode gives you the blueprint for building a support system that frees up your time and grows your bottom line.

Episode Timeline:

[0:00] – Why we’re sharing our team structure and how it helped us surpass our 2024 goals

[1:12] – Your time’s highest and best use: start there

[2:03] – The difference between hiring and strategically outsourcing

[3:09] – Using DISC and Predictive Index to assign the right roles

[4:25] – Core roles in your REI team: who we rely on every day

[5:44] – Attorneys: eviction, litigation, contracts, trusts, and why you need all 4

[6:59] – Mortgage lenders and creative financing partners

[8:02] – Title companies: what they do and why they’re critical

[9:31] – Hard money and private lenders: how we structure these deals

[11:12] – Contractors and trades: how to vet, test, and protect yourself

[12:49] – Why we use U-Haul over dumpsters for cleanouts

[13:55] – Property managers and their role in systematizing rentals

[14:38] – Local realtors and off-market lead sources

[15:49] – Our Facebook group and networking: finding your people

[16:32] – You don’t need full-time hires—just reliable, aligned partners

[17:20] – How this team structure keeps our business scalable

5 Key Takeaways:

1. Your time is your most valuable asset—build a team so you can protect it.

2. Use personality tools to place people in the roles they’ll thrive in.

3. You don’t need a huge payroll—just reliable pros in the right seats.

4. Creative financing partners and attorneys are non-negotiables.

5. Your network is your shortcut—connect, post, ask, and stay visible.

If this episode helped you rethink how to structure your business, rate, review, and follow The Real Estate Ride. Don’t go it alone—build your A-team and scale with confidence.

In this episode, Jay and I reflect on how our vision for life and business has evolved—and how we intentionally build a real estate business that fuels our freedom, not just our finances. We unpack how thinking creatively about resources, like boat or airplane clubs, shifted our mindset away from ownership and toward lifestyle design.

This conversation dives into why your calendar should reflect your values, how to move closer to your ideal life using “waypoints,” and why waiting for retirement isn’t the answer. We also talk candidly about creating multiple streams of income and real-life examples from our community of how people are aligning their goals with their daily choices.

Episode Timeline:

[0:01] – Why time—not money—is the most valuable asset

[0:42] – How our vision work turned dreams into actual calendar items

[1:59] – The boat ownership mindset shift and what we learned from boat clubs

[3:07] – Why we started exploring airplane clubs instead of private plane ownership

[5:27] – What this all has to do with designing a life that fits you—not the other way around

[8:02] – Our “Florida test run” and using waypoints to validate vision

[11:04] – Case study: laundromats, seller financing, and building cash flow creatively

[13:35] – Setting health goals with measurable steps and long-term focus

[15:28] – Short-term rental strategy targeting travel nurses

[18:44] – Why we prefer paying interest to individuals over banks

[25:01] – A discussion on hedge funds, portfolio debt, and what we’re seeing in the market

[33:59] – Comparing your income to others—and the real definition of success

[36:39] – Building multiple businesses and staying focused on your version of wealth

[43:48] – How a camping trip in Hawaii became a lesson in resourcefulness

[45:21] – Final encouragement: calendar your vision, write it like it’s already happened

5 Key Takeaways:

1. Design your business to serve your life—not the other way around.

2. Waypoints help you test your big dreams before going all in.

3. You don’t have to own everything—use clubs, rentals, and partnerships to live your vision now.

4. Creative cash-flowing assets (like laundromats or STRs) can support long-term freedom.

5. Writing your vision as if it already happened helps it become real.

If this episode helped you reframe how you think about time, income, and lifestyle design—please rate and review The Real Estate Ride, and don’t forget to share it with someone who’s ready to start building freedom today.

In this episode, I walk you through how Jay and I find and structure creative financing deals—without relying on banks, credit checks, or big down payments. If you’ve ever felt stuck because of limited access to capital or credit, this episode shows you how to make real estate happen anyway.

From $10 purchases to lease options and land trusts, I unpack the exact ways we acquire properties using seller financing and subject-to strategies. I also break down how we talk to sellers, how we protect both parties, and how we exit these deals with profit and peace of mind.

Episode Timeline:

[0:00] – Why I kicked Jay off the mic today 😉

[0:42] – Our full real estate background in a nutshell

[2:15] – How we lost it all in 2005—and why we now help others avoid that

[3:20] – What creative financing actually means (subject-to, seller finance, etc.)

[3:39] – Where we find these deals: Zillow, Facebook, Craigslist & more

[5:07] – How we use bandit signs, call tracking, and smart marketing

[6:39] – What we say to sellers and how we structure the conversation

[9:05] – The $10 house we bought—and how we made it work

[10:12] – Explaining “payments for equity” in plain language

[11:26] – How we protect sellers and ourselves with land trusts

[13:27] – Due diligence: utilities, inspections, and title checks

[15:16] – Why maintaining seller relationships post-close is critical

[16:01] – What we do after acquisition: tenant vs. tenant-buyer

[17:29] – How we structure lease-option agreements for tenant buyers

[18:09] – How we price deals and work with future homeowners

[19:08] – Why vision drives our whole business model

[20:11] – Building a plan backwards from your goals

[21:14] – Creating your power team to support creative deals

[22:36] – What your market allows (and why that matters)

[24:22] – How to balance time vs. money in your strategy

[25:44] – Hiring your first helper (even just 10 hrs/week)

[26:07] – Why vision-focused planning has kept us consistent for 20 years

[26:52] – Free checklist offer & where to get it

5 Key Takeaways:

1. Creative financing gives you a way to buy without banks—if you understand the seller’s needs.

2. You can find great leads for free if you know where to look (and how to follow up).

3. Land trusts and lease options protect all parties while creating real profit potential.

4. A strong seller relationship and clear communication are your best closing tools.

5. Your business should be built around your vision—not just chasing the next deal.

If this episode sparked new ideas for how to grow your portfolio creatively, share it with a friend who needs to hear it. And as always—rate, review, and follow The Real Estate Ride so we can keep bringing you real stories, real tools, and real estate done your way.

In this episode, we walk you through the exact framework we use to run successful rehabs—from small cosmetic flips to full gut jobs. Whether you’re brand new to flipping or scaling your renovation projects, this is the system that keeps our projects on budget, on time, and profitable.

We break down how we determine scope, organize trades, avoid common contractor delays, and create detailed estimates—before swinging a single hammer. If you’ve ever felt overwhelmed by rehab planning, or struggled with unknowns mid-project, this episode gives you the step-by-step clarity you need.

Episode Timeline:

[0:00] – Intro to the Rehab Masterplan and why you need one

[1:04] – The first thing we do before building a budget

[1:58] – Walkthrough videos: how they help you quote fast and accurately

[2:40] – Why order of operations is critical to avoid job site chaos

[3:20] – Our template: flooring, paint, kitchens, baths, HVAC, etc.

[4:35] – Creating line items with quantities and prices

[5:08] – How we group scopes for labor bidding efficiency

[6:27] – What we include in our full estimate (line by line)

[7:01] – Avoiding scope creep with early decision-making

[7:49] – The “wants vs. needs” list and why it protects your budget

[8:35] – Adding 15–20% contingency to every project

[9:12] – Why you need multiple crews or backup labor plans

[9:44] – Coordinating permits, inspections, and timelines

[10:31] – Why material pre-orders save time and money

[11:22] – What to document weekly to avoid miscommunication

[12:04] – How to evaluate when to DIY vs. outsource

[12:51] – Sample budget breakdown from one of our flips

[14:18] – The key numbers we track on every project

[15:07] – How this plan fits into the larger BRRRR or flip model

[16:03] – Final thoughts on being proactive vs. reactive in rehabbing

5 Key Takeaways:

1. Start with a detailed scope video—before bringing in a crew.

2. Pre-plan your order of operations to avoid costly delays.

3. Budget line-by-line with both labor and material separated.

4. Scope creep kills profit—know your “needs vs. wants” up front.

5. Always build in a contingency—15–20% protects your margin.

If this episode helped you simplify your next rehab, be sure to rate and review The Real Estate Ride. And don’t forget to share it with a friend who needs a better game plan on their next flip.

In this episode, I share a very personal and practical walkthrough of how Jay and I built our real estate business around our life—not the other way around. If you’re working 60+ hours a week, struggling with boundaries, or feeling like your business is your entire identity, this conversation is for you. I unpack how vision, boundaries, and intentional scheduling gave us our time back—and how you can do the same.

This isn’t theory. It’s what actually helped us go from 80-hour weeks to 12 weeks off per year, from chaos to clarity. I also break down one simple but powerful calendar exercise that changed everything for our family, our marriage, and our business.

Episode Timeline:

[0:00] – Why vision matters before business even begins

[1:13] – Our life before: Jay working 80 hours, 4 young kids, no balance

[2:07] – Realizing we needed to design our life and business together

[3:11] – The myth of hustle: why boundaries are more powerful

[4:34] – When you’re always available, you’re never fully present

[5:18] – How overwhelm sneaks in when you lack clarity

[6:10] – Why we plan our lives like people plan weddings or funerals

[7:03] – The calendar exercise: your week, your way

[8:12] – My top 3 non-negotiables for our family and business

[9:59] – You don’t need a full-time hire—start small

[10:39] – The shift that brought back Friday night date nights

[12:30] – Reframing client expectations and reclaiming time

[13:20] – Time is more valuable than money—and it’s non-refundable

[14:08] – Knowing your “genius zone” and outsourcing the rest

[16:03] – Starting with $9/hr help and getting more life back

[17:05] – If you have a day job, here’s how to start your RE biz

[18:20] – Find others who’ve built the life you want—and study them

[19:13] – Tell someone your goal. Accountability changes everything

[20:07] – Challenging the 9–5 mindset: why wait 40 years to live?

[21:03] – Coaching, meetups, masterminds—we use them all

[24:00] – How we went from burnout to 25-hour workweeks

[25:27] – Our yearly reset using the “Wheel of Life”

[27:00] – My audacious fitness goal—and what it taught me about vision

[29:08] – Reverse engineering your goals into daily steps

[30:02] – How we stay connected to our vision daily

5 Key Takeaways:

1. Don’t build a business that breaks your life. Design both together.

2. Clarity and boundaries are the secret to reclaiming your time.

3. You don’t need full-time hires—start with just a few hours a week.

4. Your calendar reveals your values. Block the time that matters.

5. A strong vision gives every task meaning—and prevents burnout.

If this episode gave you clarity, please share it with someone who’s in the thick of hustle. And don’t forget to rate, review, and follow The Real Estate Ride—it helps us keep bringing you raw, real, and helpful conversations like this one.

In this episode, we break down the 7 critical factors we evaluate before buying a flip—regardless of the market, neighborhood, or exit strategy. This is the exact checklist we use before making any flip offer, and it’s packed with lessons we’ve learned from doing this for over two decades.

If you’re trying to avoid costly mistakes, surprise delays, or deals that turn into dead weight, this one’s a must-listen. We share stories from past flips that didn’t go as planned, and exactly how to budget, inspect, and plan better on your next project.

Episode Timeline:

[0:00] – What this episode is about: the 7 things we check before every flip

[0:25] – Why you don’t want to flip next to a hoarder house

[1:13] – How one neighbor’s mess cost us two years of rent delays

[2:16] – Neighborhood red flags: crime, sex offenders, and neglected yards

[3:50] – How to budget for fences, landscaping, and visual barriers

[4:20] – Rental-heavy neighborhoods: flip them or skip them?

[5:08] – Rehab timelines: why speed and neighborhood trends matter

[6:00] – What delays gas, power, or inspections—and how to avoid it

[6:52] – Holding costs, contractor availability, and supply chain issues

[7:48] – Why you need a 15% cushion for unknowns

[8:04] – Coordinating trades and managing a reliable project schedule

[9:25] – Are you acting as the GC—or paying someone who is?

[10:17] – How to add value through layout changes and creative renovations

[11:39] – Turning formal dining rooms into master suites

[12:00] – Creative additions: patios, garages, and mini-splits

[12:36] – Checking the comps: how many, how recent, how similar?

[13:37] – What finishes and photos tell you about the local market

[14:30] – Days on market, pricing trends, and market timing

[15:00] – Your action step: pull a property and evaluate it today

5 Key Takeaways:

1. Always walk the neighborhood—don’t just look at the house.

2. Rehabs take longer (and cost more) than your contractor promises.

3. Plan for surprises—behind every wall could be termites or worse.

4. Don’t assume you can flip anywhere—comps and neighbors matter.

5. A 15% contingency and strong scheduling will save your profit.

Links & Resources:

• Tools mentioned: Zillow, Rentometer, MLS, Realtor.com

• More on our process: JayAndAnnieAdkins.com

If you found this episode helpful, share it with a friend, rate it, and leave a quick review. Every flip starts with a smart buy—use this checklist before you commit.