Jeremy Shapiro

Jeremy B. Shapiro is a serial entrepreneur and the founder of Bay Area Mastermind. In his role as mentor and coach to entrepreneurs, Jeremy has helped small business owners make the transition from “solopreneur” to “business owner”. Since 1998, he has been helping entrepreneurs discover the core strengths in themselves and their businesses, and realize their true potential, combining passion and expertise to grow their businesses and attain the freedom they deserve.

What is your typical day, and how do you make it productive?

One of the benefits of being in a Mastermind Group is Accountability. At each meeting, members commit to what they’ll be working on over the next month. These accountability items can range from strategic to tactical.

These “action Items” are then shared with the group and we check in during the month.
The last thing you want to be doing as a business owner is putting out fires all day. Having a bigger picture view of what will “move the needle” in your business sets the target of what really matters day to day.

My team and I then use Jira to manage our work in Sprints (we follow Agile / Scrum).
Day to Day, I use a personal “Daily Flight Plan” that I write the day before as I wrap up my day. It outlines the three items I’m working on first in the day, what appointments/meetings I have, and what other “Unimportant” items I’d like to get done.

How do you bring ideas to life?

We all have a good idea of what we know we don’t know.

The real opportunities for growth, however, typically come from what we don’t know we don’t know. We all have our trade groups where we can go to see what everyone else is doing that we, too, can do if we want to be just like them.

In our carefully curated Mastermind groups, however, we intentionally have a diverse range of businesses from different industries. This allows for what I like to call the “Cross Pollination” of ideas.

This is where the e-commerce business sees the success of a local retail business using direct mail and starts advertising using direct mail. This is when the attorney leverages what they learn from the online business seeing success with SEO.

This is how a B2B business takes the subscription model being used by an online education business to add automatic recurring revenue to its bottom line.

Our Mastermind Group is where the big “aha” moments come from, get refined, tested, and launched.

What’s one trend that excites you?

I love the trend I’m seeing of business returning to being more human. There was a trend of businesses trying to automate their way out of interacting with customers and as a customer it’s infuriating.

You’ve seen this with dumb chatbots, phone systems that don’t connect you to a person, emails that come from addresses you can’t respond to, and more.

Businesses got into the habit of putting barriers between themselves and their customers. Thankfully, we’re seeing businesses actually differentiate from the competition by putting customers first again and meeting their customers where they are.

This is as simple as picking up the phone when a customer calls. Allowing customers to text the phone numbers you call from – and empowering your team to respond. Being available by Instagram DM, Facebook Messenger, WhatsApp. And more.

At the Bay Area Mastermind (and in many of our member’s businesses), we use FuseDesk to bring all these channels into one place where real humans can then convert prospects and support customers.

What is one habit that helps you be productive?

Physical health is hugely important to me and helps me focus my “work” time. Most every day I either ride my road bike outside, go for a run, or hit the weight room. Fresh air, movement, and social time with friends keep me fresh and focused on the tasks at hand.

What advice would you give your younger self?

Very early in my career I had an IT consulting business and cell phones were a new thing. I was dating my now wife then girlfriend and we were out for dinner. Whenever a client would call I’d pause our date and answer the call. (Horrible, I know. I was young. Mobile phones were new. Clients were critical to the business. I’ve learned!)

At one point, on one of our earlier dates, I stopped and asked myself “What are you doing? You’re out on a date with this amazing woman and we’ve made the time to get to know each other here. How is a client call more important than this?”

From that moment forward, once it hit “after work” hours or weekends, I simply didn’t take client calls or view work emails. The next morning, or on Monday morning, etc – I’d promptly take care of whatever needed my attention and took wonderful care of my clients.

I effectively “retrained” my clients that I’m not available in the evenings and weekends and not to expect to hear back from me until “business hours”.

It was the healthiest thing I could have done and clients respected it. I was way less stressed and was able to be far more present. And more importantly, I got to know the most incredible woman in the world!

Looking back, I’d have told myself far earlier to make time for what matters. Businesses are meant to support your life; Your life isn’t meant to support a business.

Tell us something you believe almost nobody agrees with you.

The Hustle mentality is overrated. The idea that “while you’re sleeping, your competition is eating you alive” just leads to burnout and stress.

There are way too many gurus out there touting their 17-hour work day and how if you’re not “busy, busy, busy” and “grinding” and “hustling” you’re a slacker and don’t deserve to succeed.

That mentality is hugely fear-based, unsustainable, not enjoyable, and a crap way to live. It is possible to take time off from your business. For example, taking 3 months off when a child is born, traveling the world, vacationing in remote areas, and more. In fact, if you can’t do that, you likely don’t have a business.

So disagree with me all you like. But if you can’t afford to spend time with family, travel, volunteer time in your community, and actually enjoy life, why do you have a business?

What is the one thing you repeatedly do and recommend everyone else do?

Make the time to step back and work ON your business – instead of just IN your business.

This means spending time on strategy and bigger-picture work to actually grow your business and get out of working in your business.

For me, this comes in the form of monthly Mastermind Group meetings, quarterly planning meetings with my team, annual planning offsites, end-of-day daily flight plans, and dedicated time working with a business coach (yes, the best coaches have coaches themselves!).

You didn’t get into business to have a glorified job with all the risks of owning a business. Your goal should be to own a business – not just work for a paycheck. That takes conscious work, planning, and implementation.

When you feel overwhelmed or unfocused, what do you do?

We all have those moments where we feel overwhelmed or have a hard time focusing. When that happens to me, I take a step back and switch to a different part of my brain.

This typically means getting outside in some sunshine and fresh air, playing with my kids, or playing for a bit on the piano.

Before coming back to my desk, I make sure I have clarity on what needs to get done.

I also love all things coffee – especially the hustle and bustle of a cafe. At times, I will note down the 1-3 things that I need to get done and head off to a cafe without a charging cable for my laptop. If possible, I won’t even connect to the WiFi.

With no distractions and a very clear short list of what needs to get done before I have to be back home, I get done what needs to get done.

Regarding overwhelm specifically, I have my aforementioned Daily Flight Plan that is informed by our Sprints which are planned from our Annual and Quarterly Planning. It allows me to look at the overwhelmed and ask “Is this what’s most important right now? If I work on this instead, what am I going to remove from my list for today or from the Sprint?”

What is one strategy that has helped you grow your business or advance in your career?

Leverage the wisdom of others who’ve “been there, done that.” There’s no prize for reinventing the wheel or learning things the hard way. One of my favorite parts about being in a Mastermind Group is that you have 10 other people around the table from you who have spent the past month working ON their own businesses and learning what works – and what doesn’t work.

They then spend their precious time sharing their lessons and takeaways with the group and YOU get to benefit from their findings!

You get access to the vendors they recommend and have worked with. You get recommendations for the tools they’ve found that is working well for them. You find out the books that are making a difference in their business. You learn the results of their marketing experiments. And so much more!

It’s like having a virtual lab running and paying for its own experiments and then reporting back on the results to you – at no expense or investment of your own time or resources!

What is one failure in your career, how did you overcome it, and what lessons did you take away from it?

There’s the “wearing all the hats” archetype of the entrepreneur who is doing everything from being “chief cook to bottle washer” and that for me is very indicative of a “technician” being self-employed – and not yet a true business owner.

Early on, I falsely believed that a business owner is like a one-person shopkeep and is meant to do everything in the business. That’s not sustainable. And leads to burnout.

It was only when I started hiring and building out my team did I start moving to become a business owner.

Hire a bookkeeper. Hire an accountant. Hire customer support. Hire “technicians” to do the work ON your business. Hire management to RUN the business. If you can’t afford to make those hires, you can’t afford to pay yourself to run the business and you don’t have a business. You have a job.

What is one business idea you’re willing to give away to our readers?

Oh, goodness, there’s no shortage of good business ideas. I often look at what I as a customer want and where there is an opportunity for that to be solved in the marketplace with customers who are willing to pay for it.

That last part is critical.

If your idea is something that’s “nice to have” but nobody is willing to pay for it, that’s not a business idea. It’s just a wish.

When I was launching one of my software companies, it was filling a gap in the marketplace for one of my other businesses. I had shopped around looking for a solution for my business and none of them fit the bill. So I wondered if I should just create a product to fill that gap.

Unsure of the need for it, I mentioned the idea to a Mastermind Group that I was in, and multiple members all said “Yeah, it’s a terrible business idea, but can I pay you to use the software?” Ha!

So, there were willing paying customers who valued the solution as much as I did! I launched that business and had to pay customers with recurring revenue from day 1!
What business idea should you pursue?

Content is so important right now for businesses and finding quality writers who can not only create a proper editorial calendar, but can also write original good content that I’d want to read, and then publish and distribute is near impossible.

I’ve tried hiring so many writers and agencies over the years and have been continually disappointed in the garbage quality of what’s out there in the marketplace. And I’ve been astounded at freelancers and agencies that have made hundreds of thousands of dollars to multiple millions of dollars writing crappy fluff that isn’t worth reading and delivers no real value.

There’s a huge opportunity in the marketplace to write quality and original content that will bring value to people’s inboxes on behalf of your clients. Start a content agency, hire quality staff writers, create editorial calendars for your clients, write well-researched and cited pieces that deliver value, distribute them via their social media channels, and make it all “done for you” for your clients. Charge a monthly or annual subscription.

Let me know where I can sign up when you launch!

What is one piece of software that helps you be productive? How do you use it?

We follow the Agile / Scrum methodology as a team and our team uses Jira to manage our tickets and our Sprints.

By managing our backlog, we do the work that matters most first, know when it’ll get done and can commit to it.

What is the best $100 you recently spent?

My wife and I enjoy Date Night out almost every week. It’s our time to connect outside of the house as a couple without also being parents for an evening. That involves paying for childcare and a nice evening out, but is so worth it to have some quality “us time.”

We’ve done everything from just a nice dinner and a stroll around town, axe throwing (her idea, so fun!), a yoga class, an escape room, trivia night, and more.

The important part is that we get to just focus on each other, have fun, and connect.

Especially the unstructured time, like on our after-dinner strolls, the conversation just flows. Her perspective on all things is so great and so deeply appreciated. Even as it relates to business, as an entrepreneur, it can be easy to start solving a problem with one perspective. Her asking insightful questions and offering her differing perspective is so helpful to ideation.

Do you have a favorite book or podcast from which you’ve received much value?

There’s not “one” book, per se. However, I’ve even compiled a list of our Mastermind Master Reads along with our biggest takeaways from each book. I consider these “must-read” books for entrepreneurs and founders.

This list includes (among others): Think and Grow Rich by Napoleon Hill, The E-Myth Revisited by Michael Gerber, The Goal by Eliyahu Goldratt, and Traction by Gino Wickman.

What’s a movie or series you recently enjoyed and why?

I really enjoyed The Wandering Earth when it first came out and even though it was shattering global box office records, nobody stateside seemed to know about it. And then when the sequel came out recently – The Wandering Earth II – again, so many people had no idea that it even came out or what it was.

We saw it on the big screen in those D Box seats that vibrate and move with the movie and it was just so epic. It was THE way to see a larger-than-life epic sci-fi movie.

While a bit far-fetched in a dystopian future, I love how in the films the world comes together to work on a common problem for the benefit of humanity. Humanity tackles solar system-sized problems collaboratively despite human nature and individual challenges.

Key learnings:

  • How to tell if you’re truly a business owner – or if you just have a glorified job
  • When you should “hustle and grind” – and when you should focus on what really matters
  • How to prioritize your year, quarter, weeks, and even day – and the tools I use to do it
  • The best way to leverage the results of a free virtual laboratory running dozens of business experiments
  • Where to find the same old recycled ideas – and where to find the big game-changing industry-defining “Aha” moments