Welcome to the #IMadeTheAsk entrepreneur spotlight series, where we share the stories of entrepreneurs and small business owners who have made the ask…and lived to tell the tale.

Read on to learn about Jess’s business journey, how taking the chance on making an ask lead to major ROI, and why failing is most definitely not fatal.

Tell us a bit about yourself, and your journey as an entrepreneur.

I’m Jess, an award-winning graphic and web designer, and video coach for service-based business owners. I started Jess Creatives seven years ago, and after three years of side hustling, I took my business full time! Now, I spend my days helping businesses rock it online through design, strategy, and video.

What’s an Ask that you chickened out of making…and regret?

I had a podcast a few years ago, where I interviewed other female entrepreneurs about their journeys in business. I think the first regret is chickening out about not asking certain entrepreneurs to be on the show, because I thought they were too “famous” for me. But, after one particular interview, my guest and I got to chatting. You could call us “internet friends” – we occasionally comment on each other’s stuff, but that’s about it. She graciously said if there was anything she could to help me, to just ask! Well… I didn’t say anything. I was too chicken to ask for support, for shares – anything. I know that she would have helped if I had asked, and could have potentially gotten me more exposure or new connections. Who knows what could have been!

What’s the Ask that you’re most proud of making – whether or not it worked out.

I pitched myself to be on an entrepreneurial podcast that has a huge following. They seemed interested, and we did a pre-interview call – basically to see if they really did want to interview me. In the end, they told me (in sort of a rude way), that they didn’t want to interview me. I was so nervous to pitch myself, and it didn’t end well. But, I was reminded that hearing no is not fatal. (And, I’ve been on several podcasts since then!)

having the courage to negotiate can lead to big wins and strong ROI Jess Freeman.png

Which Ask has been the biggest win for you – professionally or personally?

I was a guest on a health and wellness podcast – my target niche! (Are you seeing a trend of all of my ‘asks’ yet?) I’m easing into targeting more business owners in this niche, so not many of my features or much of my own content is really targeted to them yet. I was lucky enough to get an interview on the podcast, and out of all the interviews and features I have ever done – this one had the biggest ROI by far. I had a huge jump in followers, email subscribers, and the best part, was some new clients!

What’s your #1 piece of advice for other entrepreneurs or business owners who are gearing up to #maketheask?

Don’t be afraid to put yourself out there. You will get rejected, you might not ever hear back, or… it might be one of the biggest wins in your business! You are an expert – own it.