Ashley co-founded Ice Cream Social which NBC invested in last year. 

And today, she takes us back to the beginning of her career in 2010. 

Like many entrepreneurs, Ashley quit her job to start her own business with a personal goal for work — financial freedom. 

She was 21, and didn’t have a lot of business knowledge — but she did have drive and motivation. She would be a social media expert, when no one really knew what that was just yet. 

But someone asked her to build a website. She had some knowledge in web development and SEO. And she wanted clients, so she said yes. 

At 2 am, the night before the project was due. Ashley had a meltdown. She couldn’t figure out how to deliver on the project. She was out of money, out of time — and didn’t have the technical ability to do the job. 

She’d just had a baby, and needed the money to support her child. 

This was in the days before Google or Youtube had how-tos. It was difficult to self-teach and find the answers that you need right away.

For Ashley, the meltdown was what she needed to clear her head and find a solution. 

If she didn’t get the job done — not only would she not get the second half of her payment, but they’d probably ask for the first part back. 

Knowing Your Drive

Ashley looks back on this situation and questions the main drivers that got her through this situation. 

First and foremost, it was her baby. As a first-time entrepreneur and mum at the same time, Ashley attributes her success to her children. 

She had no support, no network and no backup plan. And she’d taken a big risk. She had to support her children. 

And she thrived when her back was against the wall. Looking back, although she didn’t do it consciously — Ashley is very aware that she would find herself in high-risk situations often. 

What’s interesting is that initially, Ashley knows that she was very financially driven — as most entrepreneurs are. 

But when it started coming in, there was a big question around whether or not that’s actually what she wanted. 

She knew there was more to it than having money. 

The Quest for Freedom

Ashley went through a period of introspection on her relationship to money, work and even tested not working to understand more about the financial freedom that she was chasing. 

As an entrepreneur, Ashley’s quest for freedom, and what that means for her offers a great insight into something that many founders overlook — desire. 

The word freedom was always present in Ashley’s goals, but the meaning changed. 

She pinpoints the origins of this in a book she read on identifying motivating desires.

From this, she understood that financial freedom was a driver for her. 

When she had kids, it became about time freedom, so she could be there for them. 

And now that her children are grown and business is flowing, Ashley sees freedom in a different light. Freedom of opportunity — to have multiple business projects, and the freedom to choose. 

Having a Personal Goal in Work as Freedom

Ashley considers herself very ambitious. And the overarching theme of seeking freedom has become a filter on that. 

She uses it to evaluate the impact of each opportunity she takes on. 

Before she agrees to a project, Ashley gets really clear on the potential sacrifices that might need to be made to see the project through.

She has a clear idea of what her ideal day is, and questions what might change with a new project in tow. If it fits in between the tasks that are important to her — she’ll do it. 

Freedom of opportunity, for Ashley, is making these choices.

Reflecting on that 2 am moment again — Ashley highlights that she is much better equipped to deal with such a situation now. Because she puts her mindset — and gratitude — at the heart of everything she does. 

We talk about

  • Her transition from “back against the wall” to freedom and gratitude
  • How she maintains her positive mindset in business
  • What she needs to support a working lifestyle

Ashley is hyper-focused on taking care of her mindset and being mindful of all the moving parts in her life to support her success.

Tune in to this episode, as she offers practical advice on how to find the right balance when things aren’t right.