Breaking Down Your Business | Small Business | Business Owners | Entrepreneurship | Leadership (business)

What’s In This Episode:

What do you believe in? Jill believes in the gut-check. Brad believes in giving in any interaction - that a client or a prospect walked away with more than they came with. Both are essential to business.

"As a business gets bigger, your gut gets disconnected with what's happening in the business." - Brad

Jared Hecht, superstar to his 11-month-old son and tech guru, calls in to talk about his new startup, Fundera. He's really proud of what Fundera has accomplished, and how they're helping people all across the country with small-business pitfalls. But he has a problem with hiring. Since the company is located in NYC, it's hard to compete dollar-for-dollar with the bigger-name companies out there (Facebook, Google, the list goes on). They want the best talent. Brad and Jill suggest that he look at the areas he can compete: the mission, the autonomy involved in changing people's lives - which you might not be getting at a major company -  and the mindset of employees when it comes to workplace culture and recognition.

"If you're able to create a fun story that your PR team will go out and tell, people will gravitate toward applying to you." - Jill

Jill and Brad then discuss the top 5 things you should never quit doing:

  • Clarifying your pitch for your business.
  • Asking for feedback. Ask differently. Ask other people. JUST ASK.
  • Getting people to subscribe to your mailing list. These people, essentially, help pay your bills. Get on it.
  • RAISING YOUR PRICES. If you're not raising your prices, you're not honing your pitch. Such synergy!
  • Oh, and then there's that thing that Jill refuses to do.


  • Jared Hecht is the CEO of Fundera, a company that is transforming the world of business finance by replacing old school loan brokers with a smart and intuitive online shopping experience. Prior to founding Fundera, Hecht created GroupMe, which was eventually sold to Microsoft. 
Direct download: Breaking_Down_Your_Business_EP_230.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

Does practice make perfect? Brad seems to think so. Not only because we practice, but because the benefit increases the more we do something. Jill agrees, especially when it comes to business: the operations and managerial tasks get easier, as well as figuring out how to pitch properly so that you get a response! In fact, that might be the difference between a bad entrepreneur and a good one.

"Good entrepreneurs pay attention and aren't mindlessly doing the same thing over and over again." - Jill

Author and teacher Kimberly Johnson calls into the show because she doesn't have enough time and she's not the best at delegating. Brad says that you need to make a list - who can do things for you? Then write down procedures. Furthermore, Jill says to put a timeframe on it. If you write down 5 things, pick the first item and say, "I'm handing this off in the next 12 hours." And when you hand things off, you're actually allowing people to share in your success.

"You're more likely to get referrals the fifth time you ask than the first time you ask." - Brad

Jill and Brad then discuss the top 5 things that are better the more frequently you do them:

E-mail marketing. The more frequently you e-mail, the more people respond.
Asking for referrals.
Communication with employees. You need to communicate more than you think is necessary.
Saying no. Do one thing, and do it well.
Oh, and then there's that one thing that business owners forget to do...
Want to know what it is? Listen in!»

Listener question:

Will asks, "Do you have any tips for taking a break from your business due to moving?" Think about your clients. Will they go anywhere? You can bring on contractors to cover some things for you. Phone calls can be done from the road.


Kimberly Johnson is the author of The Start of Something BIG:: Your Ultimate Guide to Writing a Dynamic Business Plan, now in its second edition. She founded U3I, a management and marketing consulting firm which provides business development, project management, and management/technical assistance to small, medium, and large private businesses, government agencies and not-for-profit organizations. 

Direct download: Breaking20Down20Your20Business20EP20229.mp3
Category:Business -- posted at: 12:00pm EDT

What’s In This Episode:

Brad just wants to automate things - is that too much to ask? He loves Zapier. He wants to make things better, and optimize them, and make them run more efficiently! Over time, however, business owners need to keep in mind that your business will change, along with the perspective on your business. Jill says that the more efficient you get, the more you see where you actually need to do the work... instead of letting a computer do it for you. So there may be a thing as optimizing too much (sorry, Brad).

"Sometimes I'm working on the dashboard of my dashboard." - Brad

David Feinman calls into the show and talks about what "viral" means in the video space. To him, viral means getting the audience that they want to see the product at the right place at the right time. He's got a problem, though: His pricing. Two years into his business, he's realizing that while the quality of his product is better than his competitors, he's charging less than he should be. Jill and Brad explain that he absolutely should raise his prices because that communicates to the marketplace that you're more confident in the value that you're putting out. People want high-quality stuff, and if they want it bad enough, they'll pay for it. In fact, they suggest tripling David's current prices for his new clients.

"You need to take more time for yourself. Schedule a block a week. Center yourself and make more money that way." - Jill

Jill and Brad then discuss the top 5 reasons you should quit doing things that aren't working:

Do a gut-check, and put your focus elsewhere.
You could make more money (duh).
Make room to see what really matters.
Spend more time on the big picture. Or self-reflection.
Oh, and then there's that whole thing that business owners tend to spend too much time on...
Want to know what it is? Listen in!»

Oh hey there, memory lane:

As an added bonus in this episode, Rebecca Dengrove from Rebecca's Mom Leotards calls in to follow up from her podcast episode. Her terrible 1995-era website was redesigned based on Jill and Brad's advice, and consumers love it so much, she can't keep up with current demand! A better website really is magical, guys.

Guest:David Feinman is the co-founder of Viral Ideas Marketing, where they create to inspire. They believe everyone has the right to be fulfilled, they believe in shared creativity, and in the power of defining your why. His company shares this message through the creative process and through video. 

Direct download: Breaking20Down20Your20Business20EP20228.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

Jill and Brad conclude their series on money and wonder aloud why talking about money is so weird. Jill remembers that she was offended the first time someone asked her what her money-making model was. She takes a much more private and personal approach to the topic because it's one that is a source of pride as well as a vulnerability for many. Brad thinks that if you just talked about pricing outright, things wouldn't be so uncomfortable.

Social entrepreneur Joanna Black calls into the show and talks about the impetus for starting her co-working space, SheWorks Collective. The times they are a'changing for Joanna's business model, due to the fact that the collaborative/co-working environment that kicked off her business two years ago is a bit outdated. She's trying to attract new members but finds that it might be difficult given her industry. Jill and Brad suggest focusing on community as well as possible work themes which might bring connection.

"Collaboration doesn't happen because you have a conference room or because you have a meeting. It happens in between meetings." - Brad

Jill and Brad then discuss the top 5 money hang ups business owners have:

  • Everything is too expensive. Instead, focus on what's valuable to the business.
  • Insecurity about the future, leading to either spend too little or too much.
  • "Everyone has more money than me!!!" This allows you to shirk responsibility about what your priorities should be.
  • "I don't want to pay any taxes." Think of taxes as a privilege. You made money this year!
  • Oh, and then there's that nit-picky thing about running a successful business...

Want to know what it is? Listen in


  • Joanna Black is the founder of SheWorks Collective, a collaborative co-working space for female entrepreneurs. For more than 20 years, Joanna has been a leader in social responsibility, sustainability, wellness and women’s empowerment. She has consulted for some of the world’s largest companies on corporate responsibility and purpose; co-founded Hip-E Living, one of the country's first eco-lifestyle retailers; re-ignited environmental activation as managing director of Earth Day New York. Find her on Facebook.
Direct download: Breaking_Down_Your_Business_EP_227.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

Jill and Brad take a trip down memory lane and talk about why they started their businesses. When Jill started her first business, she focused on money. Now into her third enterprise, money matters a bit less and it's more about enjoyment. Brad agrees with Jill (it doesn't happen often, but it happens!): When you have a baseline, it becomes easier to build the type of business you want.

Fun fact that we didn't know about until this episode: Vanilla custard and moisturizer have similar methods of cooking.

Katarina Stetz calls into the show and discusses how she was inspired by chemistry and her grandmother from a young age to become a skincare formulator (that's the technical term for a person who makes skincare products).

Her problem? She moved from London to Chicago and doesn't know how to build up her network of industry contacts or buyers or other entrepreneurs in her new location. Every city has a code, she says, so she wants to know how to "crack the code" of Chicago. Jill and Brad suggest going to networking organizations no matter what city you're in - and while it won't happen overnight - it gradually will result in business relationships you're looking for.

And the other important thing? If you want something, all you have to do is ask. You can't go into any industry and assume that they'll be helpful without asking.

With enough opportunity, you can even create an event of your own and look like a rockstar for bringing everyone together!

"There is a much bigger mission that I understand and a lot more satisfaction I get from not thinking every day about, 'Did I make this number today?'" - Jill

Jill and Brad then discuss the top 5 things that are more important to your business than money:

  • Customer feedback. If customers are happy, the money will follow.
  • Branding and design. A good design will keep customers coming back.
  • Paying attention to the changing of the times. Stay ahead of the curve and don't get too comfortable.

"When I take a day off, I'm actually better at what I do." - Brad

  • Personal joy and freedom. Save some time for you.
  • And then there's those folks you lean on...

Want to know who they are? Listen in


  • Katarina Stetz is the founder of NINNI, a skincare company, which began in London, UK. Katarina is from Sweden and NINNI is based on the Scandinavian philosophy of natural, simple and effective skin care; all made in a sustainable way. Katarina has a Master’s degree in chemical engineering and 10 years experience in the beauty industry. Find her on Twitter, Facebook, Instagram, and Pinterest.
Direct download: Breaking_Down_Your_Business_EP_226.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

Are you a rule follower or a rule breaker?

That's the topic of the day for Jill and Brad. They discuss if entrepreneurs are, by their very nature, rule breakers or rule followers. Both consider themselves to be rule breakers, but rule followers shouldn't feel left out: Followers are vital to entrepreneurship. (Hooray!)

Sara Lingenfelter, entrepreneur and all-around awesome person, calls into the show and asks for help with finding her target audience. This leads to a conversation about the best methods for networking using LinkedIn, Facebook, or getting feedback via Google Forms or Typeform to spread the word.

"If somebody says, 'Here's the boundary' you say, 'Let me move it for you.'" - Jill

Jill and Brad discuss money rules to follow:

  • Don't run out money. This causes suffering and exasperation that you just don't need.
  • Money gives you choices. Be prudent about yours.
  • Don't borrow money, especially if you're a service-based business.

"When you borrow money, you put someone else in charge of your business." - Brad

  • If you need money, ask for it. Send your invoices on time, follow up with those who are late paying you, or raise your prices.
  • And then there's that old saying about money...

Want to know what it is? Listen in


Direct download: Breaking_Down_Your_Business_EP_225.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

In this episode (the first in a series about that cash money), Jill and Brad talk about the things they don't know but everyone else seems to: For Jill, it's accounting. For Brad, it's fashion (thank God we just have to hear him, then, right?).

They talk with Karen M. Carlson, the "absolute best, therapeutic relaxation expert east of the Mississippi" who calls in to discuss whether some of the products she's offering should be on a separate website other than the one she has now. This spurs a great conversation about what people will be drawn to when visiting your business website (hint: keep it clear and simple).

"Wait... you didn't get into business to make money?" - Brad

Jill and Brad discuss why we don't know our numbers: we're multitaskers, not accountants. (Brad likes Zapier to help with that.)We might not even know what a P&L statement is. We're not good at tracking your time.

"You can hire people, you can ask friends to look at your numbers, you can even have machines come up with reports for you." - Jill

Entrepreneurs like to try the same thing hoping for different results (spoiler alert: it won't work). And then there's always that pesky problem about numbers...

Want to know what it is? Listen!


  • Karen M. Carlson is the founder of Be Well and Renew, and is a massage therapist and author. She offers guided meditation, and makes eye pillows for adults and children to help them to be calm, quiet and comfortable in their bodies. A new children's book, which accompanies the eye pillows, will be out soon! Find her on Twitter, Facebook and YouTube.
Direct download: Breaking_Down_Your_Business_EP_224.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

We all hear about the speed of business and how we need to be faster, but is that speed good in itself? Jill gets a bit math-y and talks sine curves and parabolas, but eventually shares that we fall into the same pattern. You start off in a big rush trying to get everything done and figure it all out, but then something changes. Maybe it's burn out, tons of success, or simply age and experience -- whatever it is, you eventually realize you can slow down. We should trust our guts more because in our anxiety of trying to be faster, we inherently know the pace we should be working at. Brad and Jill chat more about why you should ease up in the Top 5 Reasons To Slow Down in this episode and they welcome coach, speaker, and author Karen Friedman to the show. Listen in! »


  • Karen Friedman is the founder of Karen Friedman Enterprises, providers of speaker and communication training programs across the globe.
Direct download: Breaking_Down_Your_Business_EP_223.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

What was the best team you were ever a part of? Jill was part of a powerhouse team at Elektra Records; they pushed each other to be better, could make fun of each other, but most importantly, were respectful of one another. For Brad, each person on his team thought they were the worst performer so they worked hard to not let the group down. That kind of respect for each other is a big part in making a team successful. Do you already have a strong team but want to push them to go further? Jill and Brad talk about the Top 5 Ways To Get Your Team GOING in this episode and they welcome billboard visionary Matthew Olivieri to the show. Listen in! »


  • Matthew Olivieri is the founder of AdSemble, a self-service billboard advertising marketplace.
Direct download: Breaking_Down_Your_Business_EP_222.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

Do you ever get that feeling that your business is about to take off? Jill definitely knows that feeling - it's exciting and re-energizing! It infuses life into the business and even though it may not pan out, it's a sign that good things are happening. Brad used to chase that feeling but has come to realize he'd rather have steady progress instead. They also talk about the Top 5 Ways To Know That It's "GO TIME" in this episode and they share which apps they've been trying out lately. We promise Jill doesn't talk about any photo apps... sort of. Listen in! »


  • Shapr - Tinder interface applied to networking. Brad swears you don't have to immediately make out as soon as you meet in person. 
  • Lighter - It's a virtual lighter. And that's it. Jill loves it.
  • BRiN - World's first artificially intelligent business advisor. Brad thinks it has potential but isn't there yet.
  • Magic - Text-based personal assistant available 24/7
  • Legend - Easily turn text into animations
  • Light Phone - A phone that's not a computer. Jill is fascinated, Brad is not. (Get a $7 burner phone from eBay instead)
Direct download: Breaking_Down_Your_Business_EP_221.mp3
Category:Business -- posted at: 3:00am EDT