Talking to Barbara Validated So Many of My Thoughts

I’m going to tell you a story in this blog…

It just so happens to be my story.

And often times when I have a guest on my show, I’m able to have my own questions answered.

So what surprised me about what Barbara had to say, as an investor in startups, was that she pushed and advocates for people to delay taking money and get out to earn your stripes, so to speak.

And while she admits it’s like “calling the kettle black,” given she herself took a on a small loan to start her business, I think we can all agree taking a $1,000 business loan versus going to Silicon Valley and seeking $100k to start a blog are inherently different conversations.

We didn’t have enough time to examine my story and see what Barbara would have thought and done, so here it is…


My Wife and I Fought Over Investment Dollars 

I remember where I was and the details of the conversation like it was yesterday.

I remember the clothes I was wearing and I remember exactly where I was on the road to my office.

My business had grown.

Correction: My business had EXPLODED.

We grew from launch to $1.2MM in revenue and in about 36 total months.

However, the leap from $50k to $1.2MM happened in about 14-16 months.

That’s like avalanche scary growth.

And so the conversation with my wife, whom was my fiance at the time, went something like this…

Kim (my wife): Chris, you’ve worked so hard and you’re now at the point where you’re making it, why would you want to bring on investors to tell you what to do and how to do it?

Me: I can’t do this anymore. I need help, I’m buried and I have no idea how we’re going to go any further than we have.

Kim: How do you think _____(competitor will remain nameless) feels now that they don’t even have majority controlling interest in their company!?

Me: You’re right…They are making such stupid decisions and I know it’s because the investors probably just don’t “get” the industry.

Kim: Exactly, so you’re going to spend most of your time working for them when you’re the one that’s actually the expert in what you do!

Me: Yea, forget them, I don’t need investors!

[End Script]

But the thing is, we were both wrong…and we were both right!

Let me explain…

Kim has bootstrapped her own business to multiple six figures.

It’s taken her years.

At the time I’m writing this it’s been about six years.

She first got a great job as a Social Media Manager for a big REIT/student housing developer.

Soon thereafter, she decided to leave the ole 9 to 5 and do her own thing.

We strategized how she could do this and developed a plan for her to leave the job AND pitch the employer into becoming her first client.

The President thought she was CRAZY!

“Why in the world do you want to do that?” He asked…

She gave him her reasons, she had her stuff together and so he bought into the idea and she was off to the races.

She did that for a few years and grew her client base substantially.

She was grossing somewhere between $6-8k/Mo and had a very healthy business with her healthy margins.

But she was growing to hate it.

Not because she hated the work but because it’s very normal for service providers to eventually feel like they have 50 jobs instead of just one.

They end up working their tails off for everyone else with very little time to work on their own businesses.

She was maybe in her mid-twenties and so we said it was time to transition into a course creator.

We “fired” off her clients and pivoted into the business she now has.

She runs a membership community that has steadily grown over the past two years into a very prosperous endeavor.

And NOW she’s ready to ramp up and scale.

Stark contrast to my situation.

And truth be told, stark contrast to who I am as a person.

Not right or wrong, just different.

So, what works for her isn’t necessarily going to work for me.

Growth requires cash.

Scaling requires all hands on deck and then some.

My nights quickly became very short.

My days felt like eternities and yet still weren’t long enough to keep up with the rampant growth.

On one occasion, I drove the distance from New York to Los Angeles and halfway back in a matter of about 10 days!

Where there were holes to be filled, it was on my to fill them.



And Then I Became Deathly ill

I don’t say deathly ill lightly.

This isn’t an exaggeration for the dramatics and flare.

My body was shutting down.

I wasn’t going to the bathroom.

Like, literally, not going to the bathroom.

And yes, I was still eating.

It got so bad we finally realized it was out of our control and went to the Doc.

Lab results showed what we feared.

That list of ailments and problems with my body is long enough for an entirely new post in itself so let me paraphrase.

I wasn’t going to live a very long life at the pace I was on.

And my entrepreneurial aspirations?


You don’t even care anymore when you feel that bad.

I pivoted and started delegating everything I could.

I thought I would just focus on my health and bounce back in no time.

But the months dragged on and my situation worsened.

The business started to suffer.

Despite my efforts and everything I had done to prepare us for the growth we desired, it was like grabbing at the brass ring that was covered in wet butter.

And so I watched my business slowly die right in front of my eyes and with very little, if anything, I could do about it.


And Then A Miracle Happened…Or So We Thought

Around this time, I knew I had already built a machine for growth.

I had automations in place from here to Timbuktu, I had the perfect Integrator as a right-hand man and I knew where the opportunity was in the market.

I had established relationships with five of the seven major players in my space (All grossing $50MM ARR or more) and were begging us to take on more work.

But I knew I needed the help…and fast.

This time it wasn’t an option, I NEEDED investors.

Within about two months on the hunt for capital, we received an initial contract & commitment letter.

With said letter, it looked as though we’d have a $1.5MM round done in just a matter of months, barring Due Diligence.

And I remember when I received the email.

I broke down and literally cried.

The help I wanted had arrived, the lifeline appeared and all of my hard work finally paid off.

No longer would I have to slave away at this thing, fighting cash flow nightmares and making the best with what I could afford.

No longer would I have to dig deep into reserves to cover our growing expenses with a growing business.

Breathing room…best way to describe it.


Until We Ran Out of Time

Vince Lombardi said it best when he said “we didn’t lose, we just ran out of time.”

And that’s exactly what happened.

At some point I’ll go into more detail about what transpired in those months thereafter but it didn’t end how I expected, hoped or dreamed.

And to a certain degree, I felt I was now left to start over.

I’ve questioned my steps ever since.

None larger than the one to NOT take investment money.

When we exploded and grew from $50k to $500k in just eight months, imagine how excited investors would have been about what we were doing!?

These are the thoughts that enter into my mind.

Did I become a vastly more skilled and knowledgeable entrepreneur?

You bet your ass I did…

That was my MBA and I earned every last freakin penny of that.

I can talk to the best of the best and carry on a conversation…

And not just carry my weight but go toe-to-toe.

My future without this health ailment is VERY bright…I know that.

But the what-ifs, at least for the moment, continue to haunt my thoughts.

The people that worked for us…what could that have been?

The industry and our plans to cause massive disruption?

I’m so confident that plan was going to work I can feel it in my bones.



And So We Move On

Rather than beat myself up about perceived failures, I’ve opted to move forward.

It’s not healthy to linger in the past.

But here’s what I want you to take away from this post.

Everything is personalized.

My wife is sometimes scared when her business grows in revenue because she recognizes that added pressure to deliver.

In my case, I throw a party and wake up the next morning with tremors about how we’re actually going to handle the growth.

It’s just who we are..and that’s okay.

And so too should you be okay with your varying approaches.

We’ve talked at length on previous installments about the resourcefulness, mentors, mindset and everything that comes with growing a startup.

Funding is in that same conversation.

And while I’m not telling you to go off and raise money because you have an “idea,” which drives me absolutely crazy to hear people say, also recognize your aspirations and what it’s going to take.

Are you willing to compromise on rampant growth for a slow build?

Or are you trying to build the next Facebook?

I don’t think it’s that binary and I think your answer probably lies somewhere in the middle of those two paradigms.

But the point is, analyze your steps before you take them and then plan a path to execution.

If that means taking an extra six months to reinforce the foundation of the company and prepare your books for a Cap Raise, so be it!

If it means lacing up the boots and hustling for just another six months to provide yourself (AND investors) with proof of concept, go do it!

And I get it…


We don’t plan for these things.

Entrepreneurship is about as predictable as the weather report on the nightly news.

Truth be told, probably way less than that, come to think of it.

And that leads me to my final point here.


Failure is Only a Construct

In my conversation with Barbara Corcoran, it was interesting to hear how much struggle and failure played into her story.

It was as if everything she’s ever accomplished was only as the result of bouncing back from a perceived failure.

And what’s both crazy and fascinating to me is how often I hear the EXACT. SAME. STORY….

Literally everyone I respect and admire in the entrepreneurship space is a total recovering failure.

And sometimes just total and UTTER failure.

Not like we’re going to fix this but like we’re starting all over from scratch again failure.

I take those stories and it’s almost therapeutic for my soul.

But the sun continued to rise.

My health improved (vastly) and I’m staring down the barrel of soon-to-be a total clean slate!

I’ve learned more in two years than I could in a lifetime.

And so would I have sought out funding at the $500k mile marker now?


But would I have learned what I know now to do with it what is probably responsible and diligent?

Would I have commanded the same prowess to navigate growth beyond where we were at that moment in time?

That’s truly anyone’s guess.

But we have this false narrative of painting the future out to be a greener pasture.

It’s great, it’s what gives us hope.

But what we hope for isn’t always reality.

There’s no way of knowing and thus, it’s a futile exercise.

So, how do you know when it’s time to go off and raise money?

Answer: When you’re ready for it

And not a minute sooner.

Maybe you’ll never need it and build a bootstrapped empire off of a small, $1,000 loan, like Barbara did.

And maybe you’ll find yourself in the middle of a $20MM Series A in two years.

But look at yourself, your business, your goals, your current milestones and progress.

Ask your mentors and advisors.

Plan out the future with your team.

Join one of the local Accelerator Programs and really go through the curriculum like every word is life or death.

LIVE entrepreneurship, don’t just DO entrepreneurship.

And my guess, if you do all of these things and with everything you have in your soul…

If you put forth all of your effort towards this ONE thing and not the MANY things we get distracted by…

And if you KNOW your clients, the market, AND the opportunity…

You’re just going to know.

And right now, if you DON’T know, it’s likely you still have some boxes to cross off.

And if you “fail,” as I did…

The same sun will rise on you again tomorrow just as it did me.

And my guess, just as it was for me, you’re going to wake up one day and realize you just had Barbara FREAKIN Corcoran on your podcast, a rapidly growing new business that you absolutely love and everything is going to be just A-OK.

Much love, my friends.



Don’t forget to also listen to the pod!



Click Here to Subscribe to the Show: iTunes | CastBox | SpotifyGoogle Play | YouTube

Barbara Corcoran, Real Estate Mogul and Co-host on ABC’s Shark Tank, drops by to talk about the power behind your struggles and how if you learn to bounce back it can become your greatest source of success.

Today’s Sponsor: The Startup Launch Factory


Business Unusual Podcast with Barbara Corcoran





To learn more about Barbara, visit


When is it Smart to Raise Money for Startup Businesses? | How Failure Often Leads to Massive Success

Pin It on Pinterest

Share This

Share This

Share this post with your friends!