I always get really excited when I get a chance to talk with other people in the online entrepreneurship space, especially with people who I think are on the same page that I am: Honest. Realistic. Hard-working.

Steph Crowder is a really rad entrepreneur who has a background in sales at Groupon.  She was one of the first 400 employees there, which is meaningful because Groupon now has over 10,000 employees worldwide.

She climbed the corporate ladder extremely fast and my first interaction with her was a few email exchanges when she was starting her online business at MissCornerOffice where she taught other women looking to get ahead in their career.

What I’m most excited to share is focused on her current work as the Director of Member Success (aka Den Momma) at Fizzle.co (affiliate link; also a free month for you!), an online community of entrepreneurs that I belong to.

You can listen here, or keep scrolling to read more about my chat with Steph!

Steph Crowder

As mentioned above, Steph worked at Groupon here in Chicago for 5 years.  She loved her experience and got in on the ground floor, and took away a lot of experiences that have informed the entrepreneurial work she does now, such as:

• Being part of the fastest growing company in history – what to do and not to do while scaling a business


• Leadership do’s and dont’s


• Training – lots of background in adult learning that translates perfectly to the work she does at Fizzle

Why leave Groupon?

I asked Steph about what would make her want to leave something like that and work at Fizzle.

As a part of a large organization, Steph experienced a lot of the traditional things you’d think of in the tech startup world like going into an office every, being part of a large team, and she found a lot of success.  She was a leader at a young age and found more success than she expected, very quickly.

This led to a lot of other young women reaching out to her to get her advice and feedback about how they could do what she had done and Steph found that she really enjoyed mentoring them.  Having done a lot of hiring at Groupon, she was able to coach people through the interview process and it turned into a career coaching business, Miss Corner Office.

She was super inspired by a lot of the same people who inspire me, like Pat Flynn, and she’d hear stories of people just like her who had constrictive jobs, but were able to escape that and cultivate the life and family they wanted.

Steph noticed a trend that most of the people on the podcasts she listened to and the blog posts that she was reading were making a living by thinking of an idea and selling it to an audience.  Just like me (and you!), she thought to herself that if other people could figure out how to do this, then she could too.

So that’s exactly what she did with her career coaching business.  She joined Fizzle because she wanted the training and community that came with it

The Real Reason Steph Left Groupon

There seems to be this really romanticized aspect of online entrepreneurship and taking ‘the leap,’ but Steph never expresses frustration or unhappiness, the two reasons most of us want to quit our 9-5 jobs.  It comes from a place of spite or hate for your job.

But that wasn’t the case for her.

She had respect, was well liked, and had great mentors.

It wasn’t about hating it and wanting to get away from it.

Steph and her husband had talked about having a family in the future and what that looked like on both of their current career trajectories.

Once she started talking to her female mentors, she looked at every single one of them and as much as she admired them, she looked at their lifestyle and was not pleased with what she saw.

Some didn’t have kids, but others did and their husbands stayed at home with the kids.

Once she realized that she couldn’t see herself operating that way, it became harder for her to get up day after day and pretend that Groupon was going to be her career for the next decade.

It just didn’t fit with the vision that she had for her life.  And if Groupon wasn’t going to be the place that allowed her to have the lifestyle she wanted and have the family she wanted, her eyes started to wanted and she started thinking…

Pat Flynn talks a lot about his ‘why’ and walking his kids to school, a fact that resonates very strongly with both Steph and I.

That what set her out on this journey.

She had to figure out how to have super meaningful work in a way that’s gratifying to her from a lifestyle perspective.

Often times, Steph thinks that we’re taught to go out and find our work and then try to fit our values around that.  Like trying to fit your ‘real’ life into the edges of your mornings and your evenings.

Steph kept seeing more and more people that put their values first and then found work to fit into that and it was such a different concept for her.

It’s like living in the Matrix.  Once you know, you can’t go back.

Leaving Your Job Because Your Hate It

One of the other things that Steph said that really struck a chord with me was about leaving a career out of spite.

And I’ve been there.  I’ve hated my job so much that I would do anything to quit. I’d take any odd online job just to make $20 so I could start getting out of a day job that I hated.

And that was great, for a time.  That hunger is really necessary to get some people to move.

But it has a darker side as well.

What happened to me is that I latched on to the first business idea that came around.  Out of desperation, I forced the first idea that I had and it wasn’t right, it wasn’t the thing, and I didn’t love it.

I just hated it less than my day job.

Steph said that there’s some danger in hating your current situation because she’s seen a lot of people who ran to the next possible thing because they were running away from a situation they didn’t like, as opposed to running toward something else.

Every business idea is a hypothesis.  The cool thing about that is it allows you to run experiments and being detached from the outcome.

We’re so desperate for the outcome that we’re destroyed if it turns out our hypothesis is wrong.  It’s so much better to be in discovery-mode and willing to tinker around a bit, Steph says.  It allows you to pivot and be more nimble in your business versus building out of desperation.

One of the Biggest Struggles of Online Entrepreneurs

Often when people start building a business online, they’re scared to niche down.

They want to speak to everybody and are afraid to draw a line in the sand and say, “I’m about this, and I’m not about that.”

But the problem is that when you speak to everybody, you end up speaking to nobody because it doesn’t resonate with any one particular group.

I just got an amazing email recently from a guy who unsubscribed from my mailing list because he isn’t married and doesn’t have kids.  He said he loved my content but couldn’t shake the feeling that it wasn’t for him.

Perfect.

Honestly, I don’t want to exclude anybody but I want to include entrepreneur dads like you and me SO MUCH that everybody else can see who this is for.

This is the third business venture that I’ve built and I’m building intentionally.

It’s the reason I get on Skype and talk on the phone with my audience. I never assume I know what they (you!) want and so many people starting out are afraid of taking the risk or have never thought of trying.

Productivity

I’ve gotten to the point with tools like the 5 Minute Journal where I felt like I wasn’t getting any benefit out of it. I was only continuing to use it because Tim Ferriss kept telling me to do it.

However, Steph has noticed a tremendous impact tools like that have had on her life.  Additionally, she’s noticed that writing out goals for the day and envisioning that it will happen, it’s much more likely to move throughout the day with intention.

From a productivity standpoint, especially as an online entrepreneur who sets their own schedule, being accountable to the goals you set earlier in your day is super helpful.

Additionally, the 5 Minute Journal asks your to write down 3 big tasks you’ll accomplish each day.

Like Steph, I thought to myself that this was stupid. I can do 10 things per day, so why only 3?

It turns out that was the problem.  By writing out 10 things per day, I was already overwhelming myself and making it nearly impossible to do even 3 things that truly moved your business forward.

Reigning in my Hustle

Steph thinks the word ‘hustle’ is super interesting.  To some degree, a lot of us fall into the trap of how hard you hustle being a badge of honor.

That’s the burnout model, Steph said.  And I totally agree. I loved being  martyr to my ‘hustle’ and reigning that