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.