If I Were to Do It All Over Again: Lessons Learned from Experienced Entrepreneurs

On Monday, February 15, I blogged live from my New Venture Lab course, when three guest entrepreneurs shared their experiences and advice:

Carter wishes she would have worked for someone else since she’s such a “slave driver” to herself. Crummy thinks it’s a good idea to get some experience before going out on your own, but you must also follow your heart.

How different is the business today? Carter said she used to work any hours she wanted to back when she started, and it was kind of lonely being alone and making buttons by herself. Now she has her own printer, people who process orders for her, and has the ability to make policies & procedures.

All three have benchmarks against which to gauge their performance – strategic alliances that must produce results (Crummy), new ideas must uphold the mission statement (Carter), and new expenses must be justified.


“Never, ever, ever do 50-50 partnerships!” – Crummy. He and his brother once even got into a fistfight about the business. It’s great having someone else who’s as committed to the success of the venture.

D’Arcy – if you’re 50/50 and you have a disagreement, need some way to prevent it from being “stretched out. If I were to do it again, it would have to be 51/49. If a partnership is like a marriage, I’m not looking forward to being married.”

Question – Could you have done this by yourself, without the partnership? Crummy – No, I wouldn’t be where I’m at without the partnership.


Question – How did you learn about running a business without formal business education?

Carter – “For me, it was about making buttons at the start. I’m still kind of learning but feel like I’ve got a grasp on what I need to do now.”

Crummy – “I don’t believe in MBAs. Most of the serious business decisions you have to make aren’t taught at business school. You pick up discipline and decision-making. You pick it up after you screw it up [especially] if it costs you a lot of money. Business isn’t rocket science. To me, it’s all about creating new business models. How do you teach that?”


Question – “What make or break moments have you had?”

D’Arcy: “We didn’t want to spend a lot of money on marketing. We got on Time Out Chicago and WGN…the media is free advertising, and that helped.”

Crummy: “We had a make AND break moment. Unfortunately, I got a nationwide roll-out with Whole Foods [for the cookie company]. I need nationwide infrastructure and money to support it. It was a big, big mistake. It was featured on Rachel Ray, I thought I had done it, I thought I’d retire…on a beach in San Diego. And then you realize that’s not how it is. The cost of creating consumer brand awareness nationwide is a lot more than you think it is, and I didn’t want to raise money for that.”


Question – “How do you get more visitors to your web site?”

Crummy – “Anyone who is charging you upfront for search engine optimization, you should be wary about. Links, links, links, is the safest way to go. Send free stuff to bloggers and ask them to link back to your site with specific words.”


What have learned about hiring, managing, and firing people?

D’Arcy – “It’s hard. I just had to fire someone recently and I’d say you try to look at character, and you have to go with your gut sometimes.”

Crummy – “We have a pretty laid-back culture, which can be a problem sometimes. You have to have a nice balance between being demanding, execution, and creating a bit of anxiety for people. The best management book I’ve read for entrepreneurs is “Lessons in Excellence” by Charlie Trotter. I highly, highly recommend it.”

Crummy – “We fired a guy who was with us for a year and a half. I considered it our fault. Our manager should have been working with the guy to [address his tardiness issue].”


Carter – “You’re only as strong as your people.”


D’Arcy – “We have a big group of followers who come in week after week to see what we have that’s new. It’s a great way to keep people coming back.”


How did you use Twitter or Facebook? Have you turned it into a revenue-generating source?

Crummy – “It’s very difficult. What do people want to talk about? Cookies? Probably not. I’m not fooling myself.”

Carter – “We do a lot of featuring of our customers since we do custom buttons. We act like a “news source” in a way of how people use buttons. It’s been pretty good because it’s community-building. We make sure we promote customers twice as often as we promote us.”


How do you come up with price points?

Crummy – “Price points are tough. We have a surcharge for Valentine’s Day orders because our costs go up. It can make us look like we’re trying to screw somebody. But it’s really the opposite. Start off with the lowest you can go, then add your overhead, and see where you are.”

D’Arcy – “When we opened, I thought we’d focus more on quality rather than getting people in and out. We heard a couple complaints that our prices were too high, and focus on getting volume up. We’ve lowered them since we opened and people didn’t really notice. Coupons helped to get people to try the dogs and then they come back to pay full price.”


Do you have any regrets? Would you do the same business again?

Carter – “I wouldn’t have dragged my feet so much on hiring people. I would’ve given up day-to-day controls more. I have a mentor now and respect her so much, and think I should have reached out to her more.”


What support networks do you have?

D’Arcy – “I talk to my grandfather a lot because he’s owned a bunch of businesses, and [other entrepreneurs]. The nice thing about entrepreneurs is that most people are willing to talk to you. Whether it’s a restaurant owner or a car dealer, and they’ll be pretty cool about talking to you.”

Crummy – “There’s no ‘even Stevens’ out there. Either people love it or they hate it. So I don’t ask a lot of people.”

Carter – “I belong to a peer roundtable, I listen to my CPA and HR person, and have a group of friends who are business owners that I get together with.”

One comment

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s