From Idea to Business — The Leap of Faith — Financial Glass

This is a Silicon Alley Podcast transcription of From Idea to Business and Quitting My Job which originally published in November of 2019. Here is a link to the Silicon Alley Podcast website. Enjoy!

Hey everyone! Welcome to the Silicon Alley podcast I’m your host William Glass. On the Silicon Alley Podcast, we talk about what it’s really like to be an entrepreneur and what’s the actual journey. So looking at entrepreneurship not with the rosy-colored glasses of success but from the ground up.

How I went from an idea to quitting my job to start a business

Today I want to talk to you about the idea. Ostrich didn’t start off as Ostrich and we’ve come a long way. But the idea started, at this point, about two and a half years before I actually left my job to start this company full-time. So there’d been something that had been festering in the back of my mind for a while and it was about creating a better way to talk about money and finances.

The inkling of an idea

I’ve been a heavy user of Mint, Personal Capital, and Charlie and many of those money management tools that I really enjoyed. It gave me access to seeing exactly where my money was and I could check and track things and all that kind of stuff. So I really enjoyed that and at the same time, I also had some experiences where money has been a real challenge within my family.

I guess the heart of it is that my parents got divorced because of money. They never had a common language and had different philosophies and we’re never able to really talk about it. And ended up getting caught up in the real estate bubble in 2008 and over-leveraging themselves when it came to rental properties and condos at the beach. There was no real consensus as to whether they were meant to cash flow or sell for a profit. Just not being on the same page led to a lot of challenges. Now not to say that that would have saved their marriage being able to talk about finances.

Historically, one of the number one causes of relationships failure is money and finances. It’s something that we’re not taught in schools. It’s something that we’re not really taught to talk about and you learn either really good habits from your family and friends or you learn really bad ones. And that’s just kind of the way it is.

Recognizing my mission and vision for the business

For me, I think this whole idea started from that. I only realized that relatively recently after actually starting the company. That’s really where this all stemmed from, I always knew that it had something to do with that experience. But you know really analyzing why this is this stuck around for so many years. Anyway, the idea came to me a couple of years ago. I was just thinking, “I wish there was a place where I could go and just talk about money to people and have a safe place to talk about it. I could have real conversations”

Also, I wanted to find out information about how much my co-workers were being paid. Because at work we were talking about it. I worked in sales so money is at the heart of the incentive structure of any salesperson is the commissions and bonuses. So we were having the conversations to some degree but we weren’t having the underlying conversations. You can see people that were in a lot of debt that would go out and buy brand new trucks and cars. On the other hand, you’d see people that didn’t have any student loan debt and we’re living more frugally. It was interesting observing the different dynamics.

Often we had the conversation at a high level of like how much commission are you making this month and things like that. But there was still that level of hiddenness. So the original idea for Ostrich was to come up with a social media type platform or someplace where people could talk about money. I didn’t really know exactly what that looked like but I wanted to have a place where you talk about finances.

Putting pen to paper

So I wrote a business plan over the course of a day or two and went really in-depth. Then I didn’t really look at it for a while. I told a couple of people and they were kind of interested but that was about it. Then it would seem that about every couple of months I would end up revisiting the business plan. So I would look at it and make some edits. I’d think to myself “man that would be such a good idea and I wish we could do this.”

Slowly I started getting comfortable talking about it with people. Truthfully that’s where the idea really started but it took a lot of time before I got to the point where I knew this was not just a cool idea but it was something that was more important. It had a mission behind it as well as was gonna be a viable business.

People always ask, “how would you monetize it” and start asking certain questions that would lead me to start to think about each piece. Going from an idea to business really took place over the course of two years. That’s where the idea for Ostrich started.

Finding a partner in the business

Then my co-founder Andrew Holliday and I got together about five or six months before I left my job to work on Ostrich full-time. We started getting a little bit more serious. Andrew was interested in entrepreneurship and we’d been good friends since college. Being close friends, I knew that he wanted to do something more entrepreneurial but didn’t necessarily have an idea that spoke to him. Truthfully, I knew that I couldn’t do this alone. There’s a quote about building things that if you want to go fast do it alone. But if you want to go far do it with others. That is how we’ve approached the business.

Periodically we would meet and iterate on the idea. We put together a couple of pitch decks and sent around to friends and family for feedback. Finally, I just hit a point where it was like I’m not giving enough effort. I don’t have enough mental capacity to both do a really good job at my day job as well as build out an amazing company.

The decision to quit my job

At that point, that’s where I finally hit the breaking point where I was like, “okay I need to leave. I need to step away.” I’ve saved up enough cash that I can float myself for a while and still have money to invest in the business. Luckily I was pretty smart and pretty frugal in terms of how I lived three or four years prior. I had a lot of success in sales and then living frugally meant that I had money lying around that I needed something to do with.

So yeah so that’s really what it was it was just a combination of moments. It wasn’t like here’s one aha moment. Funnily enough, I recorded a video in March, probably mid to early March, saying “This is it! I’m going to quit. This is the moment.” Yet it still took me another month before I actually left and put in my resignation.

There is no right way. Only your way

Ultimately there’s no right time or answer to start your business. You’ve just got to be able to make that decision. I think it’s a lot of really small nibblings that finally get you to the point of going from idea to actually jumping ship and starting. Now I”m not saying that the way that I’m doing it is the way for everyone. There are a lot of folks and a lot of safety in building something on the side as you continue to work. A handful of folks that I talk to are doing that. They’re starting their own a “side hustle” and will transition once they’ve got some experience.

But that’s not how I work. I need to be fully focused on what I’m doing and interested in the work I’m doing. Personally I have to do a good job at whatever I’m doing. The focus is on giving it my full attention and best effort. Ultimately I couldn’t do that for my employer as well as build Ostrich. I just didn’t have the bandwidth to really make it successful. Again I don’t recommend my way for everyone but that was my thought process and what led me to go from an idea to start a business.

Gathering information on the idea and turning it into a business

Over the course of two-plus years, my really great idea kept festering. It hung around for two years before it finally turned into a legitimate business. Yet each time I revisited the idea I would get a little bit more information. I’d do more research and would start to contemplate how could you actually monetize the business without compromising the mission.

Then I’d think about what are the actual features. We’d talk to people about what they want and what they are missing right now. That process happened over time until I built up enough conviction that this wasn’t just a cool, neat, fun idea anymore but it was something that needed to happen. This business and platform needed to take place because no one else is trying to solve financial well-being the way that it needs to be solved based on the research and the understanding of people that we at Ostrich do.

That’s the story of going from an idea to starting a business. I’ll open up and say that I even hedged when I turned in my resignation. I told my manager at the time, “Hey I can hang around as long as you need to for another month and a half to find and train someone.” The company which I think made a lot of sense decided to actually accelerate my notice for which was the end of April and they actually accelerated it because of team morale. Additionally, there was a lot of new leadership and they wanted to hire their own folks so it was beneficial for all involved.

Control what you can control

My point is that you can’t draw out exactly how you leave and when you jump ship. All you can do is control your end of it. Ultimately there’s no perfect way to start.

Finally, the last piece that’s really important that helped me solidify that I needed to build this company are the things that I’d been saying. So I’ve been saying that I wanted to start a business for a while and threw around a lot of ideas. Inside I felt like a phony and like I was just one of those people that talked and never acted. That’s not how I operate. I was running different business ideas past a dear friend Vince Perez. As I was telling him about it he looked at me and he said, “Don’t start that business you don’t care. It’s just a now thing. What you really need to be doing is you need to be working on this financial platform. I’ve never heard you as excited and convicted except for this. This is what you need to do.” That solidified it for me.

Remember there’s no perfect way to know that it’s time for you to go and start your own company. Or that the idea needs to actually turn into a business. What you’ll find are a lot of little clues. And you’ve got to be attuned to them and pick them up. And finally, make that decision for yourself.

That’s it for the Silicon Alley Podcast I’m William Glass and you heard about my process of going from an idea to actually start a business. Please subscribe and let me know what your thoughts and challenges are around starting a business. Have you been getting these little signs? What’s your thought process?

Shoutout to Brett Miller for providing his song Million Voices as the theme music for this podcast. A special thanks to Karolina Gancarz for help editing and always thank you to everyone who supports the podcast and to you! We wouldn’t be able to do without you. Thanks so much! This is a Financial Glass production.

“If I keep down this path I’m gonna be miserable. Am I weighing my life based on money? Or am I weighing it based on you know being happy…”

Click here to listen to the next episode of the Silicon Alley Podcast Am I Weighing my Life Based on Money or Happiness with Cory Johnston Founder of Brighteous Media or here for a preview of the episode and here for a transcription of the episode.

Originally published at on December 11, 2019.

Entrepreneur, lifelong learner, and traveler