After losing everything in the 2008 crash, Allen Lomax rebuilt his life by rethinking wealth, taxes, and trust—and created The Great Tax Escape.

In this episode of RealDealChat, Allen Lomax shares a deeply personal story of loss, reinvention, and clarity after the 2008 financial crash wiped out everything he had built.

We explore why high-income professionals often feel trapped despite success, how taxes quietly erode wealth, and why working harder inside a broken system rarely leads to freedom. Allen breaks down his six-phase framework for becoming a capital allocator—covering trusted networks, due diligence, infrastructure, tax strategy, and disciplined oversight.

This is a powerful conversation about trust over control, systems over hustle, and why wealth is ultimately about freedom, choice, and purpose—not just numbers.

🌐 Learn More:

👉 https://thegreattaxescape.org

🎙️ Allen’s Podcast: Dreams to Impact

Call to Action:

If this episode made you rethink wealth and taxes, share it with one investor or professional who needs to hear it—and learn more at https://realdealcrew.com

Timestamps:

1. 00:00 – When success still doesn’t feel like freedom
2. 01:40 – Losing everything in the 2008 crash
3. 04:30 – Fear, shame, and starting over
4. 05:45 – The lesson from a horse named Doc
5. 07:30 – Why wealth responds to trust, not control
6. 10:30 – Becoming a capital allocator
7. 12:00 – The six-phase system explained
8. 16:30 – Taxes as the invisible wealth killer
9. 18:45 – It’s never too late to rebuild
10. 22:00 – Building trust through track records
11. 26:00 – Technology, CRMs, and AI in investing
12. 29:30 – Wealth, meaning, and purpose
13. 31:30 – Rapid fire: leverage, mindset, books
14. 33:30 – Slowing down as the ultimate time saver

tax strategy for investors, Allen Lomax, capital allocator, high income professionals, real estate tax planning, alternative investing, passive investing mindset, escaping the IRS, wealth systems, real estate syndication education, financial freedom podcast, RealDealChat podcast, investor mindset, tax efficient investing

RealDealCrew.com

We empower real estate investors by optimizing your business processes through customized automation and system integration. From lead management to deal closure, we help you build a scalable and efficient operation. Learn more at RealDealCrew.com

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when you're beaten down and you have nothing, I guess you can either live on Social

Security or you can decide to take a different path.

2

when we're talking about taxes and our incomes, sometimes we have to remember that it is

part of that strategy is how do we make money in one way it is reducing our taxes as much

3

as possible.

4

I mean that's true for all of us, but particularly individuals who are in high income

brackets.

5

are spending anywhere from 40 to 50 percent of their income without their choice and

giving it away to the IRS.

6

And that's no way to build your wealth.

7

You have to develop tax strategies if you're going to develop

8

Alan Lomax joins me here today.

9

You can learn what he can help you with by heading over to thegreattaxescape.com.

10

I'm going to have that as a clickable link in the show notes.

11

Really appreciate your time here today, Alan, as we talk about a number of things.

12

Thank you, Jack.

13

It's wonderful to be with you today and your audience and looking forward to an

interesting and enlivening conversation.

14

Well, we're going to kind of do a truncated version of this because everybody likes to

hear everybody's origin stories.

15

But you likely over your three decades of experience here now, I'm sure you're kind of

tired of telling everybody how you found your way into real estate.

16

But for those who may not have heard it, how did you find your way here?

17

Well, I expect that many in your audience are not unlike I was, hardworking, high

achieving professionals, doctors, engineers, architects, entrepreneurs, so on and so

18

forth.

19

People who've built impressive careers and are still wondering why true freedom feels just

out of reach.

20

Like me, maybe you're doctor and engineer.

21

Someone who's given years to mastering a craft and still it feels like you're galloping

hard but stuck inside some corral fenced in by taxes and time.

22

You've built your expertise, your income, your reputation, but you're still trading hours

for a lifestyle that just doesn't feel like freedom.

23

Well, I know how these things feel because I've certainly been there running

24

full speed ahead doing everything I was supposed to be doing and somehow still just losing

ground.

25

On paper, looked great, was terrific, my career was thriving and at the time my portfolio

was growing and I had a net worth higher than what I had ever really imagined that I could

26

attain.

27

So if you're a professional listening to these, you know that on paper things can look

wonderful.

28

but that doesn't mean you're escaping anything.

29

So I just worked harder and harder and then 2008, the crash hit and absolutely everything

that I had worked for and that I had built collapsed essentially overnight.

30

But really and truly what vanished wasn't money, wasn't capital, it was a sense of freedom

and I lost my self-esteem.

31

my agency, and I lost the belief that my efforts mattered and that I could make a

difference.

32

I had shackled myself with this enormous weight of shame that was truly unbearable.

33

And I built a life on intellect, on work ethic.

34

on doing everything that was right and then suddenly it all felt like it was all nothing.

35

But the most painful thing wasn't just losing that capital, it was really losing hope

because at my age, time was definitely not on my side and time is the only one asset you

36

can't buy back.

37

So that was the turning point and I think it's probably not unusual that rock bottom

points in our life are actually those major turning points.

38

I think a lot of people struggled, especially in that 2007, eight, nine timeframe.

39

And when you hit that low of the low, I mean, it just kind of your, your compass

completely goes off course, it's hard to even know if you even trust yourself, let alone

40

what you think you should be doing.

41

So eventually, and it took a long time, I found a mentor.

42

Actually, it was a mentor who never actually said a word.

43

His name was Doc.

44

Doc was a horse.

45

He was a thousand pounds of muscle, mistrust, and deep-seated trauma.

46

He'd been hurt, and fear had become his language.

47

You couldn't halter him, you couldn't really approach him.

48

He was really a dangerous horse.

49

So as I reflected on this, I realized, well, that's me, and that's where I am at.

50

So when I lost everything, it was fear that took over.

51

It was not just despair, it was fear.

52

So I started to grip tighter on not...

53

only money, but I controlled everything.

54

I was deeply into the conditioned illusion that more effort will somehow bring it all

together.

55

And I suspect many of my overworked, high achieving professional colleagues know this as

well, that we double down our effort and instead of redesigning the system that got us to

56

where we were, we

57

bring it all together with more work, which brings us more recognition, which brings us

more work, but it doesn't bring us any more money or security.

58

So what happened with me and Doc, instead of me trying to force him into anything, I just

waited with him.

59

I just stood still in silent, present, contemplation.

60

And after some 20, 30 minutes or so,

61

A shift started to happen.

62

His eyes softened, his breath slowed, he lowered his head, and I simply slipped the halter

on, which was a symbol of trust.

63

And in reflection, I understood wealth is really much like horses.

64

It doesn't respond to control, it responds to trust and to confidence.

65

You can't force it.

66

So you have to create conditions for it.

67

And that moment with Doc became that foundation for everything that followed.

68

And eventually, for me, it's what brought about the great text, Escape.

69

And it has changed everything about how I thought and what I had built next.

70

the great tax escape.org.

71

What would people find there?

72

what's the end goal?

73

Well, the end goal is, of course, for professionals to stop exchanging their time, effort,

and energy for money and to build and to utilize their incomes to build capital, to build

74

the lifestyle that they truly want.

75

There's a number of different ways, of course, to get there.

76

think certainly one of the...

77

big things about real estate and in the investment world in and of itself is that there's

all kinds of different shiny objects out there.

78

And we have to choose a path that is the right path for me.

79

And so the path that I chose was after a lot of investigation, a lot of working with

mastermind groups and different people, having my own podcast.

80

I finally realized that the thing that I really need to be doing was to become essentially

what is a capital allocator.

81

And so what I did is I put together a six-phase system that is the anatomy of how others

can do this very same thing.

82

And this really began a five-year journey to building from scratch because I was in a

situation where I didn't have a choice but to build from scratch.

83

If you're a high-income earner, you've got capital and you don't necessarily have to start

there, but that was where I essentially had to begin from.

84

So phase one is what I did and it's what every rider needs is a herd.

85

So I began to build my herd with trusted people who share my vision, my values, and they

became the operators, the advisors, the fellow investors who keep me grounded.

86

I learned the hard way that independence without trust is

87

just essentially isolation.

88

So after the crash, I rebuilt from scratch and I began building a network.

89

I've met with over 750 different operators, vetting each one until I found the handful

that I can work with integrity and who have a strong presence themselves and they know

90

what they're doing.

91

So.

92

Anyone's freedom will rise and fall with strength of the herd.

93

And if you're a doctor, a professional or whatever, you probably already built a network

for your career.

94

So you know how to build networks.

95

What you probably haven't done is to build a network that helps you to build your capital.

96

And so that's the missing piece for many of us.

97

And then phase two is

98

really detecting the true stallions.

99

Not every opportunity deserves our presence in our saddle.

100

And that's why I built what I call the Dill Stallion Detector, and it's a 53-point due

diligence framework that separates the true thrill-breds from imposters.

101

So in this phase, it probably speaks to those of you who are disciplined in your

professions already.

102

So you know how to do that, but what you need is a system that takes you to where you want

to be and takes you through that due diligence process.

103

And phase through is designing the range, which is the infrastructure.

104

You need an infrastructure, the ecosystem, the entities, the banking systems, the

reporting, the CRMs, the funnels, the...

105

investor portals, the management portals.

106

All of these tools are essential really to any aspect of real estate investing, but

they're absolutely critical to capital raising if that is the path that you want to

107

choose.

108

So you can think of it like an architect.

109

Financial designs are built for stability and beauty, just like an architect builds

110

uh actual physical structures.

111

So phase four is to run through the open range and this is the vehicle that puts it all

together and what we use is a special purpose vehicle that's designed for clarity and

112

compliance and it gives us the necessary control to accumulate capital and put it to use

in a way that helps our investors

113

to get better terms, better returns, rather than working individually.

114

So you put it all together and it protects and also gives the IRS uh strategies that help

you to reduce your tax liability.

115

And phase five is to guide with the compass.

116

And this...

117

is the Wells Dalyan campus, Compass, and with this it is the mechanism for alternative

investing.

118

It's an educational program that relieves the anxiety that helps people to move forward

who've never invested in alternative assets to do so with knowledge that gives them the

119

confidence and the security to move forward that they need.

120

And finally, step six just keeps it all together.

121

And this is the system that ensures consistent oversight, course correction when needed,

and gives us the metrics to reserves and to performance and to monitor all of that in a

122

way that makes sense for us and our investors.

123

So that's where the magic is, is really in the system.

124

So that's where I got to, that's where anyone who wants to can essentially do the same

thing.

125

Well, I think it's quite remarkable.

126

Most people would bail ship at that point where they're, where they were having the level

of problems you were in, that timeframe.

127

But in the end, looks like what you did was just kind of doubled down, build out the

systems and learn from that experience.

128

I guess if I'd had a choice to go a different way, I probably would have.

129

But when you're beaten down and you have nothing, I guess you can either live on Social

Security or you can decide to take a different path.

130

And so I decided that just wasn't for me.

131

But it wasn't like I was working alone, like I was developing that network.

132

It was very encouraging network.

133

mean, for instance, some of you may know Lee Yoder.

134

He was a physical therapist in the healthcare field, worked hard at that, enjoyed his

profession, enjoyed what he was doing.

135

But like me, he had realized that there was another way to go about it.

136

And so he moved into multifamily.

137

and developed a multi-family portfolio and is now living a very different kind of life.

138

Or Fernando Angelucci, who was an engineer, the same thing.

139

He looked at his profession as an engineer and goes, this is great and this is wonderful,

but there's a cap on your income no matter how high that income is.

140

He took responsibility for that and utilizing his engineering background, he learned how

to do cost segregations, bonus depreciation, tax strategies to utilize that in the

141

self-storage phase.

142

And he's put together a technical framework that has given him the freedom.

143

So we could go on with different examples like that.

144

So it wasn't just me, but I had the examples of other people, other kinds of mentors,

other than just Doc the horse there to help me take me through that.

145

So we take different paths and different professionals.

146

We realize that when we're working hard,

147

ah and working harder than ever but still fenced in by the IRS and structures that really

were not built for building wealth, then we can find our way out of those and we can find

148

a way to run free.

149

It's a simple truth, but it can change everything.

150

It can change the course for any one of us.

151

Just to remind everybody, if you like what we're talking about here so far, I would

suggest you check out Alan's website, go to the great tax escape calm.

152

That again is going to be a clickable link in the show notes.

153

It's important to note that this show only grows if you share it with an investor friend.

154

So consider doing that.

155

And if you're on watching us on YouTube, give us a like and subscribe.

156

So Alan, you're kind of a uh

157

just a correction there.

158

It's it's dot org rather than docked dot com.

159

Yes, no problem

160

escape.org.

161

I'll have that as a clickable link in the show notes.

162

Alan, you mentioned, you know, now, because of, well, let's just face it, the because of

your age, you felt like you didn't really have a choice, you could either live on Social

163

Security or double down and figure this out.

164

I think it's given gives a lot of people in a similar situation, you know, like it when

when I got into real estate investing, it was simply because I realized there was no way

165

for me to save to any kind of retirement, you know, in my W two, it just just wasn't going

to be possible, especially knowing how much you would actually need.

166

Like, it's just a good example of you either react to pain, or

167

over any kind of gain.

168

what, could you talk a little bit about battling through that mindset?

169

And it just gives us, gives people the inspiration that it's never too late.

170

Like you could turn this around and you could really kind of find a path here towards some

sort of retirement.

171

think uh part of that had to do with my history.

172

mean, before 2008, I was investing in real estate and it was amazing.

173

I mean, my net worth had grown substantially.

174

I had freedoms I never dreamed that I would have.

175

And so I had had that experience.

176

under my belt and I knew what that felt like.

177

And I knew that I wanted that back.

178

It wasn't just that I didn't want to live on social security.

179

I already knew what it was like to have the freedom and the choices to do that.

180

And I think that that...

181

Knowledge made a huge difference when it came to the fact that I had to start all over

again.

182

I knew that I had done it once.

183

I knew that it was possible to do it again.

184

But it was also just that terror of living in that confinement of social security.

185

I mean, there's people...

186

who find tranquility and happiness in doing that.

187

I just wasn't going to reconcile myself to this is my life because it was, and it's not

the money, it's the choices.

188

It's the freedom, it's the opportunity.

189

And I plan to live a very healthy life and

190

until the day I die and so I want choices and opportunities.

191

I don't know if that answers your question or not.

192

Yeah, no, it does.

193

Because, like I said, you know, it's just one of those things.

194

I think social security is one of those situations where it's, it's, it's a lot of people

kind of resigned themselves to the fact versus anything else.

195

It's almost a form of giving up financially.

196

I don't know how else to put it.

197

And maybe maybe I'm miss miss speaking in that regard.

198

But

199

There's a large chunk of the population that end up in that situation.

200

So.

201

they do.

202

And I mean, part of that is that they've never been taught that there are options.

203

They've never really been able to see beyond what's traditionally been put in front of

204

Yeah, it's a they don't know what they don't know type situation.

205

Yeah.

206

It's much like you know, when I when you said your domain name, the great tax escape.org.

207

That's a that's a great example of this because the if you want to call it the 1 % or or

whatever there is there's a number of people that are playing this this game that

208

normal, most people just aren't aware of like, it's it's I compare it my wife mentioned it

just the other day again, how do farmers make money, they don't spend it.

209

When when we're talking about taxes and our incomes, sometimes we have to remember that it

is part of that strategy is how do we make money in one way it is reducing our taxes as

210

much as possible.

211

I mean that's true for all of us, but particularly individuals who are in high income

brackets.

212

are spending anywhere from 40 to 50 percent of their income without their choice and

giving it away to the IRS.

213

And that's no way to build your wealth.

214

You have to develop tax strategies if you're going to develop wealth.

215

You know, when you were building, you could use the example from from the first time

around to the second.

216

What has been one of the most challenging aspects of all of this?

217

You gave us that list earlier.

218

But were there any of those that are like some of the more daunting or harder, the harder

to kind of get over?

219

hardest was getting out there and developing a network that was truly the most challenging

thing, particularly given the state of my mind and that I felt like at that point in time

220

I really had no self-worth and I certainly had no network financially.

221

And it was just challenging.

222

It was the most challenging thing was deciding I am going to put myself out there again.

223

And I did it by doing a podcast.

224

those first episodes, I would hate to go back and watch them.

225

They were pathetic.

226

But the...

227

The about them, it was a terrifying experience to open myself up to that and to begin

doing that process.

228

So terror was the big challenge there, is just coming over that, overcoming that terror

and just getting out there and doing it.

229

It was the biggest challenge.

230

After that, everything else has fallen into place.

231

oh without a great deal of difficulty.

232

mean, my background is in organizational systems and so building systems comes pretty

naturally and I've had a lot of experience doing that.

233

So I was putting myself out there and building that network.

234

Hands down, that was it.

235

It was just for having to face your peers again.

236

What was the hold up there?

237

Was it typically you blowing this?

238

I don't want to say out of proportion, it kind of, sometimes it seems like the people in

our network are a bit more welcoming than we give them credit.

239

It was me.

240

The issue was me.

241

It was an internal issue.

242

I I put up all those fear barriers.

243

were, I mean, everybody from the get-go, everyone who was on my podcast, as terrible as it

was to start with, were...

244

were supportive, kind, helpful in every way, shape and form you could think of.

245

The obstacle was not the people, the obstacle was me, myself and I.

246

You mentioned earlier part of your, picking your stallions was, was to make sure that the

people were acting with integrity, I think was what you had said.

247

Was there something that happened that kind of burned you in the previous run that made

you kind of fortify that piece of it?

248

Not really, but it is just that in meeting with some 750 people, you just begin to realize

that people have different skill sets.

249

And I wouldn't say that really, that narrowing it down to the people that I'm working

with, not necessarily that people are not trustworthy.

250

I think by and large, most people are.

251

But there are people who are just better established and who have track records to show

that they're established.

252

so trustworthiness doesn't have to rely upon, oh, I think this is a good or this is a bad

person.

253

The trust comes from

254

seeing what the track record is, knowing what their performances are, and taking that even

a step further, are they willing to show where they've failed and where they've succeeded.

255

And when they can do that, as well as show you that, we failed here, we learned from this,

that's trust building in and of itself there.

256

And so that's the...

257

In terms of what I'm talking about, in building trust, that's really what it is.

258

It isn't that anyone out there is necessarily mistrusting or not trustworthy, I guess I

should say.

259

It's just that there are operators out there who have an established record upon which I

can base my trust in them.

260

Well, this time around, did you find, you know, maybe it's just because the experience the

first time, did you find anything easier, whether it's you mentioned funnels and CRMs and,

261

some of those tools?

262

Have you found some advancements in those in that realm that made things maybe a little

easier on the technical side this time around?

263

Well, certainly in the last 10, 20 years.

264

well, really the last 10 years, there has been a lot of advancement in the development of

CRM tools.

265

You know, probably 20 years ago, I would have had to have done all of that on a

spreadsheet, and that's pretty challenging to keep track of that.

266

Transitioning from that to online CRM's is like the difference between night and day.

267

So yes, absolutely that makes it easier and then in the last couple of years the AI

applications have simplified so many many processes and integrated things that were

268

Isolated from one another and pulling those integrations together

269

simplifies so much about the entire systems building.

270

So yeah, that's much easier than what it would have been some 20 years ago, that's for

sure.

271

So if somebody goes to the great tax escape dot org, what type of information would they

find

272

Well, there's a couple of things there that, you know, some people may find themselves in

the situation I was in.

273

You may have to build it from scratch.

274

And so that's probably really not the place for you, but if you have some capital and

you're willing to learn how to take that capital and to invest that capital, there's a lot

275

of things that we can do for you if you go to thegreattaxascape.org.

276

So for professionals who are busy,

277

In the healing profession, designing, building, or leading, whatever it is, the system

does the heavy lifting for you.

278

You don't have to start from scratch.

279

It's the accumulation of every lesson I've learned, every structure, every vetted operator

and system that I've built.

280

And by going there, we'll help you break free from the IRS corral.

281

and help you to let your wealth run wild.

282

And we do that through education.

283

We do that through bringing these operators together, putting together the special purpose

fund of funds where we can collectively put capital together so that when we go to these

284

operators, we get better.

285

better terms, better returns for our investors than what they could do going directly to

the various different operators.

286

So it's an educational system, it's investment opportunities, and when it comes down to

it, more than anything else, it's a mentoring uh system that helps you take the education

287

and helps you overcome those personal obstacles, whether they're fear, whether it's

anxiety, whether it's just making those decisions.

288

Is this the investment or is this the investment?

289

There's a mentoring process there for everyone.

290

Well, Dr.

291

Lomax, this has been a great conversation.

292

Again, I'm going to direct everybody to your site, the great tax escape dot org.

293

You said you had a podcast.

294

What's the name of that?

295

Streams to impact.

296

dreams to impact.

297

I'll try to find that and put that as a clickable link as well.

298

So you can subscribe to Alan's podcast there.

299

But before we jump into the rapid fire and close out this episode, is there anything else

we should have tried to hit on?

300

Well, you know, there's just not time to hit on everything.

301

But I think that one thing that I always like to touch on, and that is really what is

wealth for?

302

And is it just to spend money or?

303

what is, what's really our purpose, what's our meaning, and how is it that we can take

that wealth and help us to thrive and to flourish.

304

And Martin Seligman's research really points out that there's really five aspects to a

life that flourishes and that the

305

Perma and it's just it's positive emotions, engagement, relationships, meaning and

achievement and bringing more of those into our lives gives us just the why for which we

306

develop all of those, all of our wealth financially.

307

Yeah, that's one of those recurring things in our in this podcast is is establishing your

why because it's the only only way to to drive you it's either pain or having a strong

308

enough why in which to drive towards.

309

Well, sir, this has been a fantastic conversation.

310

Again, it is the great tax escape.org.

311

And if you're ready, we'll jump into the rapid fire and close out this episode.

312

I'm ready.

313

What lie do real estate investors often tell themselves?

314

I think it's hard to narrow that down to one line.

315

There's so many.

316

I guess one of the big things is you can never have too much leverage.

317

Then rents will always increase with value add.

318

The exit cap will always be lower than the entry.

319

Appreciation will take care of everything.

320

With a good property manager, short-term rentals can be passive.

321

And so all kinds of lies that we tell ourselves in real estate.

322

And I've done all of them, so I know.

323

I know.

324

I've been there.

325

If you could go back in time and give your younger self a piece of advice, what would it

be?

326

it would be just be you.

327

In the end, that's all we really have is ourself.

328

And if we can't be true to ourselves, what do we really have?

329

So yeah, just be you.

330

And I wished I had learned that at 20 rather than 40.

331

Do you have a book recommendation or what are you reading right now?

332

Well, yeah, I've got several.

333

Carol Dweck, the mindset is terrific.

334

And because without a mindset, we're just not going to grow.

335

And Angela Duckworth, Grit helps you to put that mindset to work.

336

And for investors, Brian Burke's book, The Hands Off Investor is a fundamental,

understandable book, real well-written book.

337

for investors to really start understanding alternative investments.

338

And finally, what process or tool have you implemented that has had the biggest

time-saving impact?

339

Well, you know, when I first thought of this question, I thought, well, chat GPT.

340

And then I thought, no, that hasn't really saved me any time.

341

It's just given me the ability to cram more things into the time that I already have.

342

So really the time saver is when I really learn to slow down, to become mindful.

343

And I found this in the presence of Doc, and that is just to be presence and to appreciate

every present moment.

344

And that's where the time saving is really at.

345

Well, this has just been fantastic.

346

One last time, the great tax escape dot org clickable link in the show notes.

347

Really appreciate your time, sir.

348

This was fantastic.

349

Well, it's been wonderful being with you, Jack.

350

Wonderful podcast you have, and I've really enjoyed it.