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Explaining to my Dad why I quit my job

May 19, 2013 - Posted in Business , Family , Startups , Uncategorized Posted by:

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Monday May 20th will be the very first day that I work for myself, full-time, on my start-up. There are plenty of variables to worry about when starting a new business but what I was most worried about was telling my father that I was going to quit my “good” job. The prospect of generating traction didn’t terrify me, and the innovative product was almost complete, but I was dreading the “talk” I had to have with my dad.

It doesn’t seem crazy to me

My parents live in Florida (of course) and I was holding the phone to my ear waiting for my dad to come on the line from their house. When he came on the line I just blurted it out…

“Dad I’ve decided to work on my own business full time.”

I let it hang on the wire, waiting for the blistering response about how I was letting my family down, and exposing my kids to unnecessary risks. I had imagined how he would lecture me on how hard he and my mom worked so that I (and my three little sisters) could get a college education, and how I had no right to throw it all away on some silly dream about starting my own business. And, about how my wife deserved a husband who would make good adult (not risky) choices about my career.

I had imagined how he would remind me about my long days at a full-time job and long nights spent in class to earn an MBA from a top school. I knew how his mind worked, he raised me after all and I had been on the receiving end of such lectures many times before.

A rough road

My dad had been in business for himself once before. He and my mom opened a coffee shop on main street in the little town they lived in before moving to Florida. It was a lot of work, and they barely made any money. On many days my dad would open the store up at 4am and work the morning rush, then come back in the evening to reconcile the cash register and close the store at midnight.

No matter how hard he worked, that coffee shop was never going to generate much profit without major changes in the business model. Though I doubted he would bring up his own failures, I knew that it would influence how he approached the conversation with me.

I’ve failed before

This isn’t my first rodeo either. I’ve attempted to do a software start up before (more than once) and failed. They were not particularly private failures either. I always get so excited about my ideas that I broadcast them to everyone. I imagined that my prior failures would play into my conversation with my dad also. It would be a dose of “tough love” to bring me back to reality.

The father speaks

“Well I wish you the best of luck. I’m sure you’ll do great.”

I was stunned. I’d been so prepared to launch into a defense of my current project and my reasons for focusing on it full-time that I had never considered he might be supportive. We went on to have a great talk, about the start-up some but mostly about my kids and my sisters.


After talking to my dad I wondered how I could have gauged his reaction so inaccurately. I think it comes down to my own fears in the end. I believe I was projecting my own fears onto him, and trying to talk myself out of it without having to take ownership of the fears.

Startup Families

Does anyone else have any experience with this? What were the reactions when you told your parents or spouses or whoever is important to you that you were going to quit your job and take gigantic risks?


richard weisberger 3 years ago

What space are you developing for?

Reply 3 years ago

It serves info about Muli-Family listings over $10m. I can’t take sole credit. The other developers I am working with are here: Nebuleaf Studios


Javier Echenique 3 years ago

Hi Josh,
Great decision… You know is a risky thing and it’s harder having a family.
After many years working in several companies and some failed startups, two years ago I quit my job as manager at Oracle and started my own business, a mobile development company.
So far we have 2 years into the market and things are slowly improving.
It was a great decision because I love what I’m doing, but it’s being hard from a financial perspective, since I’m still away from my previous salary, however I expect to reach that point point towards the end of this year.
The most complicated stuff is related to family, money is never enough and some sacrifices has to be done.

The best of lucks with your new endeavour, and try harder to minimize risks.



Len 3 years ago

Hey a very similar experience earlier this year when I went full-time on my startup. Especially coming from a family of immigrants who worked so hard to get here and raise me well, it wasn’t easy (or so I thought) to explain my rationale. But over time, and by not going to into all the gory details, they understood and applauded it far more than I would have expected.

Good for you man.


Greg 3 years ago

Hey Josh!

Thanks for the post.

I’m curious, how much money did you save up before deciding to leave your job?

Also, can you tell us a little bit about your revenue model?


Reply 3 years ago

Hi Greg, I saved about 10 months worth of expenses. is essentially an information listing service for multi-family properties valued at over $10 million. These properties are usually purchased by private equity funds and the brokers listing them are unable to list them on more traditional sites (e.g. because the volume of inquiries from unqualified purchasers is too great.

So these private equity buyers each hire 3 or 4 people who call each other on the phone all day to build a list of what’s available. Needless to say this is expensive and the information tends to be old or inaccurate or both. So we pull all of the listing info together and put it up on a closed site where only qualified buyers can see it.

We charge the private equity funds to view the listings. The buyers like it because they can make decisions based on timely and accurate information and the brokers like it because we are efficiently connecting them with qualified buyers.

The system can host broker’s listing for them on the broker’s website also, and there are some other smaller revenue streams like that, but the primary one is the subscription we sell to the private equity funds.



Greg 3 years ago

Thank you for the reply, that was insightful!


Taylor Beck 3 years ago

If you are already living on your own and supporting yourself (and can continue to do so while working on your startup), I see no direct reason to be worried about what others may say. Sure, there are naysayers – there will unfortunately ALWAYS be these people – that try to demotivate you.

You are embarking on a new journey. It will be scary at times. If you keep pushing towards your goals, you will most likely eventually achieve them.

Anyway, I wish you great luck!


Erich Stauffer 3 years ago

I had four kids when I first quit my job to run my own company full time (I now have five). I too was scared to tell my dad. I actually told him about a month after I quit so I could tell him I was ‘making it’. Like you I was expecting him to yell at me, but he was supportive. It makes me almost tear up now to think about it. That was almost two years ago now.


Santosh 3 years ago

The site looks good Josh.

Did you gauge the interest in your site from investors?

I am just wondering if they are already engaged with interests with research from their “preferred” brokers on opportunities to invest into.

Where are you aggregating the content from?

Good luck!

Reply 3 years ago

Our team is evaluating potential investment partners now. It’s a little early for us to be talking seriously to Venture Capital firms, so for now we are looking at 3F money.

Typically these equity groups raise capital for their funds with a specific investment profile based on the financials of the properties. It basically comes down to if the property fits the underwriting criteria or not. The equity groups do seem to have “preferred brokers” but only due to time constraints. Currently it is simply not possible for them to evaluate all the opportunities. We aim to make it possible.

Building the data set is just a lot of grunt work. A lot of time on the phone. A lot of looking at flyers. We have some proprietary tools to consume incoming data and organize it into an easily consumable format, but mostly it’s just grunt work. If it was easy we wouldn’t be adding much value.



Bob H 3 years ago

I recently quit a senior management position in a billion dollar multinational Asian CE giant. While I didn’t jump without a net this is a bit of a risk. I am now at a company of less than 20 people which isn’t exactly thriving, my job is to turn it around and make everyone rich. My consolation is that I get the freedom to finally develop some of those ideas that the conservative multinational wouldn’t touch.

Wish you luck!


Mike Austin 3 years ago

This is exactly why you are (not will be) a success – because you are not afraid to be vulnerable/honest and that always draws people to you. That and you have been blessed with great fatherly advice. Ha!

Reply 3 years ago

Thanks Dad!


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