Crafting a Life That Fits Your Vision

Serial entrepreneur Steven Miyao has been involved in many fields, and his latest venture—a professional coaching business—allows him to guide clients toward what will make them happy and successful. He says too many professionals choose a career and then try to mold their lives around it. In this edition of “The Deep Dive”, host Jay Hummel talks with Steven about his own journey, including how he reverse-engineered the sale of his first company, Kasina. 

Steven Miyao: Steven Miyao is the founder of Coaching Metta, a consultancy designed to help clients redefine success in their lives. He has held executive roles at companies in the healthcare field, artificial intelligence, as well as financial services —including the data firm he founded and eventually sold, Kasina. Steven is a graduate of NYU and lives in New York City. 

Video Transcript

[00:00:06.33] – Jay Hummel

Hi, this is Jay Hummel. Welcome to “The Deep Dive” in collaboration with Investopedia. We often discuss investments, wealth management, and mergers and acquisitions. But we don’t talk enough about entrepreneurship, particularly in terms of how entrepreneurs think about work-life balance and how they invest in their businesses in a way that aligns with their lives and goals.

Today, I’m excited to have a good friend of mine, Steven Miyao, on the show. Steven is a successful entrepreneur, and now an executive coach, and I think he can provide valuable insights on a topic we haven’t explored much before. Steven, thank you so much for being on the show today.

Steven Miyao

Jay, thank you. I’m excited to be here.

Steven’s Entrepreneurial Background

[00:00:57.20] – Jay Hummel 

Tell the viewers a bit about your background. It’s interesting, so give us a brief overview of your history and what you’re up to today.

Steven Miyao

Sure. As you said, I’ve been an entrepreneur most of my life. I started my first company, Kasina, at 27. Initially, we were a management consulting firm primarily serving wealth and asset management companies, helping them with strategies, product development, distribution, and marketing.

In 2007–2008, during the financial crisis, things took a downturn, and I almost lost the business. Asset managers were losing 40–60% of their value, and nobody was hiring consultants. So, we pivoted and built a data business, which we later sold to DST, a publicly traded company. Afterward, I ran several divisions within DST.

Eventually, I realized corporate life wasn’t for me and transitioned to coaching. Despite that, I continued advising start-ups and often found myself back in the operator seat. I’ve had several successful exits in the process. Recently, though, I’ve decided to focus solely on coaching and advising start-ups without getting back into operations. That’s where I’m at now.

Jay Hummel

You’re not done yet though, right?

Steven Miyao

Not by a long shot.

Key Learnings from Kasina

[00:02:58.45] – Jay Hummel 

 Reflecting on your journey with Kasina—starting the company at 27—what were some key lessons you learned along the way? I’m sure there were many ups and downs, but what were some of the most important takeaways?

Steven Miyao

There are so many lessons to share. For me, it was like my business school experience. I learned through trial and error; many lessons came the hard way. My biggest takeaway is that it’s crucial to be clear about your objective—why are you doing what you’re doing?

The answer is simple for some: “This is a lifestyle business. I can work from anywhere, enjoy my life, and keep it sustainable.” But for most entrepreneurs, it’s not that simple. You’re hustling all the time, and it’s stressful.

In 2007, I had a pivotal moment when I realized I was at risk of going bankrupt. At the time, I had a young child, and I knew that if I didn’t make changes, I could end up losing everything. That’s when I decided to pivot the business and take money off the table to create a sellable company.

Jay Hummel 

A bankruptcy is not an ideal time to be looking for a financial services job.

Steven Miyao 

No, definitely not. And that’s when I realized the importance of pivoting. I sold a portion of the company and shifted our focus to data. This decision helped me avoid disaster and eventually led to a successful exit. 

You do have to think about your long-term strategy. How do you want to monetize what you’re doing? Once I knew what I had to do, I built the company around what I thought other companies could not do and wanted to integrate and buy.

I actually figured out which companies would be potential buyers. Then, I built strategic relationships with them so that we could test the idea and then they could see the value. Eventually, they came to me about an acquisition.  

I essentially needed a financial meltdown to realize that I had to take some money off the table and that the status quo no longer worked for me.

Jay Hummel 

Well, you reverse-engineered it, right?

Steven Miyo

Absolutely.

Making the Right Moves

[00:07:00.99]- Jay Hummel 

Most of our viewers are financial advisors. How would you advise the viewers of this to take what you learned in your entrepreneurial journey to what they may be dealing with daily?

Steven Miyao

Many entrepreneurs wait too long to sell their companies. They overvalue them and assume that by staying longer, they’ll increase the value or get a bigger exit. However, the reality is that the longer you wait, the more risk you’re taking.

When an opportunity to sell arises, look at the offer objectively. Don’t get caught up in the potential for a higher price in the future. Ask yourself if the offer will change your life—if the answer is yes, then that’s a significant event worth considering.

Coaching Insights

[00:09:19.65] – Jay Hummel 

I’ll pivot a little bit here on our last topic: You’re doing a lot of coaching, right…executive coaching, spending a lot of time with RA owners, tech owners, etc. What one or two things are you coaching these executives on today?

Steven Miyao

I think the most important thing is this: Most people pick a career, and then they try to fit their life around it, meaning their spouse, their children, their friends, their faith, etc. It should really be the other way around. You should try to figure out what you want your life to be and then try to find a career that enables you to live that life. And I’ve tried to do that, at least in the last five years. 

We also discussed the fact that most people don’t live very deliberate lives. They don’t actually think about,  “What do I want the outcome to be?” and put a plan together to execute that. So, if you plan to sell your business at some point, think about how to sell it and what you need to do. 

The third one is that if you don’t plan your time or decide how you use it, somebody else will. Many people are always busy, and they can never get all the things that they want to.

These things are so logical. And it’s so easy to coach other people, but it is so hard to take your own advice. I’m bad at it, and I’m lucky to mentor many younger people in their careers.

Closing Thoughts

[00:14:10.13]] – Jay Hummel

Well, Steven, this has been awesome. You continue to make a huge impact on people in the industry. I can’t thank you enough for coming on the show.

Steven Miyao

 My pleasure, Jay. 

Jay Hummel

How do people find you?

Steve Miyao

The easiest is probably on Linkedin, and of course, my website, coachingmetta.com. My podcast is called Midlife Remix.

Jay Hummel

Well, I’d encourage the viewers to reach out to Steven. We look forward to seeing you next time on “The Deep Dive.”