Breaking Down Your Business | Small Business | Business Owners | Entrepreneurship | Leadership

What’s In This Episode:

Christmas is over, but Jill's not giving up on making eggnog a year-round thing. What are the things they loved most from the holiday? Jill's still basking in the hugs from her daughters (and eggnog), while Brad's happy about the slippers he received.

"If you spend all your time on your personal brand, then the business can never really move away from you." - Brad

Eric Paul Olson, chief marketing officer for Clever Stilettos, an online magazine for women entrepreneurs, calls in to discuss his dilemma. He can't figure out what he wants to devote time to -- his personal brand or the Clever Stilettos brand. He has a team of eight people to help him run Clever Stilettos, but he runs a podcast to go along with the magazine. Furthermore, Eric's also an actor on Chicago Fire and Chicago Med, so Brad and Jill suggest that maybe he should hire someone to help him with Clever Stilettos while he focuses on acting. Jill says that hosting a podcast is great, but he needs to hand it off to the team once he's done lending his time to it. His team can promote on all sides - both the Eric Olson brand AND the Clever Stiletto brand. Brad says that some fans of Eric Olson, the actor, will be interested in the fact that he ALSO has a digital marketing interest. Basically, it comes down to knowing who your audience is and distributing content accordingly.

"I want to pay more attention to my space next year. I used to care less about clutter, but I need more space now." - Jill

Jill and Brad then discuss the top 5 non-money-driven goals for next year:

  • Try to be more present. No technology (phone, laptop - put it away!) - spend some more time with your family instead.
  • Taking more time off.
  • Make your workspace work better for you.
  • SAY NO! Get out of the habit of saying yes to everything.
  • And the number one thing? It's a tough one, but anyone can join in...

Want to know what it is? Listen in


  • Eric Paul Olson is the chief marketing officer of Clever Stilettos, a women's entrepreneurial magazine. He splits his time between podcasting and acting
Direct download: Breaking_Dwon_Your_Business_EP_238.mp3
Category:Business -- posted at: 2:00am CDT

What’s In This Episode:

The end is near! The end of the year, that is. And, as the year draws to a close, Jill's in love... with a pitch. She appreciates a pitch she received via email was so personalized via audio that she could tell the person really put time and effort into it. Brad had the opposite reaction: he disliked that he had to click and figure out the message, and thought the sender could have just written things out.

"Why would I listen to two minutes and thirty-six seconds of yapping?" - Brad

Frank Ford, author of Happy Accidents: The Transformative Power of "YES, AND" at Work and in Lifeimproviser, and owner of Four Day Weekend, a comedy space in Fort Worth, TX, calls in to discuss how to open up a new location. He has the opportunity to open up a second location in Dallas, but wonders how to bring the quality and the value to the new digs. 

Brad says to replicate exactly. Once you can get the quality up to par, then you can innovate. Secondly, he suggests that Frank doesn't have to work with entirely new staff. Transfer some over from the original location so the feel and vibe are there. Thirdly, he says that Frank can follow the example of the Blue Man Group and reconvene frequently to see what's working for best practices.

Jill says face-t0-face meetings will be invaluable. And to keep structure, but don't have hard-and-fast rules. Think of SNL, she says. The structure has been carried through for decades and the brand is apparent, but everyone has done it a little differently.

"Take some freakin' time off!" - Jill

Jill and Brad then discuss the top 5 things you need to do before year end:

  • Look at your taxes. Do it. Do it now.
  • Make a budget. Set goals.
  • Acknowledge those who make your business run. Say thank you!
  • Take some time off.
  • And the number one thing? It's a fun one...

Want to know what it is? Listen in


  • Frank Ford is the owner of Four Day Weekend, a comedy institution in Texas. In addition to performing in over 5,000 shows and working with Fortune 500 companies throughout the world, Frank is also a very popular keynote presenter on the speaker circuit.
Direct download: Breaking_Dwon_Your_Business_EP_237.mp3
Category:Business -- posted at: 3:00am CDT

What’s In This Episode:

How long is a long break? In some industries, Brad says, you can take a really long time off. College professors can take sabbaticals. Some professionals can take up to three months! What does Jill think of that? Genius idea. It never hurts to give your brain a break. It's helpful every time. Could Brad take a year off? Well, he could, but he wouldn't have any income. But he's trying to incorporate some sort of sabbatical into his routine. He's going to try it and report back. Good luck, Brad!

"As somebody who's taken time off, you'd have to plan in advance. But there's a way to manage it so that it's doable." - Jill

Ruben Ocampo of Conic, an innovation consultancy, calls into the show to ask how to diversify his client base. For years, he's worked with Fortune 500 companies, but now he's looking to also work with smaller companies and non-profit organizations. He's worked really hard to market his brand, and it's finally starting to pay off. But where does he take the business from here?

Brad wonders, "Well, if you were one of your clients, what would you tell them to do?" Ruben has a clear vision of where he wants to go, but he's trying to work out the path to get there. He knows that he doesn't have to focus on the little things in business (he has an employee to whom he can hand off tasks!). Ultimately, he wants to establish himself as a thought leader.

The good news is that his business is doing well, so Brad suggests that if he wants to take on a business partner, he has to be careful because partnerships can be tricky. If he wants to become part of a larger company, the advantage is that he can get access to larger clients, but he needs to get to know the culture first. Find a place that will value his creativity. However, he might get the largest traction for his ultimate goal by just simply reaching out and saying that he's available for speaking and writing opportunities, and looking for possible projects to collaborate on.

"Saying no to this one is saying yes to the next one that might work." - Brad

Jill and Brad then discuss the top 5 ways to plan for a long break:

  • Hire a virtual assistant or a part-timer to work remotely for you. Look at UpWork or IVAA or Founding Moms and keep things running!
  • Collaborate with someone in your field. Have them take the lead and cover for each other in periods of absence.
  • Utilize technology: have your technology take care of technology for you. Use Zapier or Drift. Auto-responders are magical.
  • Have a team? Teach them to handle things!
  • And the last thing? It's so easy...

Want to know what it is? Listen in


  • Ruben Ocampo is the founder of Conic Group, a strategic innovation consultancy, established in 2011. He works with clients in different industries, from Fortune 500 companies to nonprofits and government agencies. He uses a unique approach to engage clients in meaningful conversations with their customers, workforce, and other key stakeholders in the value chain. This approach allows teams to create and deliver intuitive, empowering, innovative and delightful experiences that translate into healthier business results. Find him on Twitter and LinkedIn.
Direct download: Breaking_Down_Your_Business_EP_236.mp3
Category:Business -- posted at: 2:00am CDT

What’s In This Episode:

Did you ever work with a workaholic? Jill did, and it was not fun. Brad considers himself to be a recovering workaholic, and now operates under the assumption that if you don't answer e-mails right away, the world won't end.

Michael Asare of FeeBelly calls in for help on how to convert the free users of his app to paid users. Jill suggests that Michael is giving too many keywords away on the free version, and so he can cut back on that and offer more information on the paid version. Brad says that for a B2C user who doesn't need to go through pages of loan documents every month, it may be worth it to have a one-time price for one document instead of someone who doesn't want to pay for a monthly subscription.

"Get some rest so that you can be more creative." - Brad

Jill and Brad then discuss the top 5 ways taking time off makes you a better business owner:

  • You might be less of a work-addict. Addicts don't make good leaders.
  • Getting away gives you perspective and realize what's actually important.
  • Taking breaks makes you more creative!
  • When you take time off, you have to delegate.
  • And then there's that thing that's pretty irritating to those around you...



  • Michael Asare is the founder of FeeBelly, an app that allows you to scan documents for the hidden fees that are often in the small print. It is available for download from the App Store.
Direct download: Breaking_Down_Your_Business_EP_235.mp3
Category:Business -- posted at: 2:00am CDT