Jeff: Done in 10 Years.

I met Jeff through a neighbor. He was a blind lunch date. He says he decided he liked me when I told him up-front I didn’t like to bake nor did I care much about cupcakes. I decided I liked him when he didn’t use any frilly business BS with me.

Between the time we met and now, Jeff has taken his superstar status to a whole new level with Insight Labs. He’s worked with a lot of really big names and has gotten the ball rolling with a ton of organizations to make changes for the better. (I participated in a lab discussing how to effectively merge retail with tutoring/education.)

So, at lunch today, I asked him what direction Insight Labs was headed. He gave me a list of “here’s what we’re doing,” and then said this:

“Howell [one of his partners] and I were flying to a lab one day, and decided that we would be done with this in 10 years. It has changed the way we approach everything – since there is now a deadline for everything we want to accomplish.”

If I approached my business with a drop-dead date, would my bucket list of desired business accomplishments be a lot more ambitious? Probably. Would I act more aggressively? Yes. Would I waste as much time as I do now? Definitely not.

Jen: Lost & Found Taxi Cabs.

Jen and I met at some networking/party event in River North last year. When I met her, I was like, “OMG! You’re Jen Chicago! You look just like your Twitter avatar!” (Nerdy.)

Fast forward. I got a call Monday night from a friend who left his wallet in a cab. So, as any good friend would do, I googled “LOST WALLET TAXI CHICAGO.”

The first search result? This post by Jen Chicago: Lost & Found Taxi Cabs.

Pictures of every cab +
Phone numbers to each cab company’s lost and found departments =
Brilliant.

I do not hesitate to acknowledge that without this blog post, I’m sure that my friend’s wallet would have been lost in cab-land for the rest of time.

Thankfully, we called two of the cab companies, and, 2 1/2 hours later, found the lost wallet. Hooray!

So, Jen, thank you for posting this and for making it so easy to track down every single cab company in Chicago. I’m sure I’m not the only one who’s ever used that post as a resource.

Fabulous.

Melissa: 10 minutes.

I went to a party last year, which was a total dud. The only good thing to come out of it? My introduction to and friendship with Melissa. (Which made the event totally worth it.)

Melissa is a fierce, bold, action-oriented, passionate entrepreneur/idea girl/supermom/friend. She decided she wanted to make a film, so she did. She decided she wanted to start a company, so she did. She decided she wanted to interview Seth Godin, so she did. Why not.

I admire everything about her.

She joined me and a couple of girlfriends for lunch the other day. I think we were talking about website domains that she bought for fun. And she said, “If an idea is good enough to stick around for 10 minutes, then it’s definitely worth the $5 it costs to buy the domain for it.”

So basically, don’t waste time. Act.

I should do more of that, and less of what I’m good at: procrastinating.

Thanks, lovely – as always.

Genevieve: Sales > Marketing.

I spoke at an event called Entrepreneurs Unplugg’d a few weeks ago alongside power entrepreneurs like the founder of GrubHub, Crowdspring, and ConstantKarma. (I don’t know why I was invited to speak, but thanks Tim and Stella for thinking I could play with the big dogs.) Genevieve Thiers, founder of Sittercity.com, also presented her start-up story.

Her presentation, in addition to being so super informative, high energy and fun (and operatic and theatrical), had one major key takeaway for me:

When starting a business . . . when you’re doing the stuff to get rolling . . . sales are key. Sales are more important than marketing. Because without sales, you can’t continue marketing.

Super easy concept. Super difficult for someone like me to keep in mind, since I think the marketing stuff is so fun (and the sales part is not as fun).

I’m so glad to have Genevieve as an example of someone to look up to. Thanks, lady, for inspiring me!

Debbie: Power Hour

If you’re like me, you get distracted by phone calls, emails, Facebook notifications, Tweetdeck chirping in the background, a 4 year old who wants yogurt or string cheese or candy or cupcakes, a buzzing dryer, online Sudoku, blogs, Google calendar, the need to shower, etc.

My former business coach Debbie taught me that each distraction actually takes 4 times as long to tend to, which is why she told me to start my Power Hour: focused, non-distracted work time to get through things that are critical for maintaining business. I go to my office and shut the door with a little post-it that says “Working” on it so everyone knows not to interrupt.

I break down my daily Power Hour into four 15-minute segments. (I do 15 because I’m so ADD to begin with; anything longer would require way too much brainpower. )

1. Reply to e-mails. DO NOT OPEN TWEETDECK, FACEBOOK, OTHER BROWSERS. (SO super challenging.)
2. Make outreach business building, focused phone calls. I hate making phone calls, so often I’ll bribe myself with shoes. (For every 100 phone calls I make, I get to buy a new pair of shoes. )
3. Strategize. I’ll focus on different areas daily, such as operations, marketing or networking. A 15 minute timeframe makes me think critically and acutely.
4. Learn. I’ll read an article, a chapter out of a business book, blog post, etc.

What are the four areas in your life you need to maintain daily? And what would happen if you could do them without being interrupted?

Debbie, I love you for making me create my own power hour. My life is infinitely more productive, serene, and less cluttered by distractions. LOVE YOU FOR IT.

Fabrizio: Bastardo team!

En route to Barcelona from Nice in 1999, I shared an overnight train cabin with Fabrizio and his Italian buddy, two South African girls, and a French guy. Kind of like speed dating, we rotated through the cabin to talk and pass the time. Fabrizio and I immediately started talking about the World Cup, which the French had won the previous summer.

“You know why the Italians didn’t win? They should have won. Italians are the BEST (hands in the air) at football, but they still didn’t win. Bastardo team; they didn’t take it one game at a time.“

I started laughing, but he was really upset (as any good European soccer fan would be).

What he wanted me to understand: take it one game at a time. Don’t get overconfident. Don’t let one loss mess up your psyche. Regroup after every game. Assess weak spots and work on them until they’re strengths. Don’t set your sights to be World Cup champions until you’ve done all the prep work.

I bet Fabrizio is happy they’re the current FIFA champions.

Bastardos. Hilarious.

Scott: It’s tough to be productive with a guilty conscience.

Nate introduced me to Matt who introduced me to Scott (@chicagojones), with whom I lunched a few weeks ago. Great conversation, smart guy, runs his own ad agency, lots of prominent clients – in short, he’s brilliant.

A few days ago, a colleague sent a link to Communication Arts magazine (which I hear is pretty prestigious), and I was scrolling through the Insights section. Lo and behold, they featured Scott. So I started to read.

While the interview is charismatic and entertaining (and Scott has great responses to every question, so you should read it regardless), I LOVE this:

Q: What’s your approach to balancing work and life?
A: No matter how many hours you put into work, it’s always going to be there; I have three kids who won’t be young forever. Since it’s tough to be productive with a guilty conscience, I try to knock things out when it matters least to them—before they wake up or after they’re in bed.

I often always feel guilty. But being guilty does nobody any good. I need to move past the self-imposed guilt, be productive when my kid doesn’t care that I’m busy, and be intentional when I do get spend time with him.

Great insight, Scott. Next lunch, I’m going to pick your brain about how you balance it all so well. Here’s to late night/early morning work hours, Diet Coke and brilliance.

Tom: Relationships + numbers = fun.

Tom Krieglstein (@tomkrieglstein) is one of my new favorite people. Among the many things on his list of accomplishments, he owns and operates SwiftKick – providing the training and tools to student leaders to engage others in their college experiences.

He invited me and Nate to his presentation on Dance Floor Theory at UIC. While his speaking style was engaging and his content captivating, one thing that stood out as absolutely brilliant was this:

“Anything is fun with relationships and numbers.”

It doesn’t matter how well-planned your event is. If it a) is not attended by enough people and b) doesn’t allow people to bond based on their common interests, chances are it won’t be fun. And fun is memorable.

I need to remember this, not only among my company’s internal staff relationships, but also among customers. I’m positive people across Chicagoland could really connect via their love for cupcakes, and with numbers, they could do something amazing for the community. I’m not quite sure what this could be, but I’m definitely open to just about anything right now. As long as it’s fun. And legal.

Does anyone have any ideas? (And thank you, thank you Tom! You’re so FAB!)

Stacy: I’m not sure why I never tried this!

Stacy and I have known each other for a little over three years. She’s cute. She’s small. She’s concerned about other people’s welfare. She’s friendly. She’s a fire survivor. And to top it all off, she has six kids.

ALL BOYS.

She just posted this on her Facebook wall with the comment, “I’m not sure why I never tried this!”

Stacy, I give you my personal permission to do this whenever, wherever. You’ve earned it.

Matt: I just worked really hard.

I recently was treated to lunch by @mbgusa (coordinated by @ItStartsWithUs… thanks, Nate!) and determined that Matt’s decidedly THE most down-to-earth Chicago trading firm CEO / nature photographer I’ve ever met, because of this conversation:

—-

Me: So what got you into trading?

Matt: When I was young, I met someone who was a trader. I thought it looked like the most fascinating thing I could ever do. I said I’d do it someday. I got an entry level job at the Boston Stock Exchange. I didn’t know anything about the industry. But I watched and I learned and I took risks. And I just worked really hard.

(Okay, so that’s a bit of a paraphrase. But that’s the gist.)

—-

Matt’s such an example to me of smarts, intuition, and awareness of those around him. And to top it off, he’s so incredibly humble and insightful that you really know he’s as genuine as can be.

Thank you, Matt, for a great lunch conversation. And thank you also for inspiring me.