How to Win a Business Competition: Tips from an Entrepreneur

Fellow marketer, have you included winning awards as part of your brand strategy? If you’ve wondered if it would be worth your time to enter business competitions, here are behind-the-scenes tips on how Comma Copywriters won a vote-based award and the real effort it required.

How we won the “Fan Favorite” Award

This is Crystalee Beck, founder of Comma. When Comma Copywriters was named one of 36 finalists (out of 200 entries!) in the RevRoad 2020 Entrepreneur Competition in Utah, I set my sights on winning the “Fan Favorite” Award, which included a $1,000 check reward.

More than a bonus check, the goal for Comma was visibility. I liked the idea of using the business competition as an awareness campaign for Comma and getting valuable practice pitching in person. (The contest was both for real-life pitches and the vote-based award.) I figured I had a better shot getting votes than in the pitch portion of the competition. Here’s exactly how we won it — and I’m sharing so you can win one yourself!

First, you’re going to need to ask, ask, ask for help. Second, you’ll need to dedicate time to getting votes —whether it’s your time and/or your team’s time. I decided I would not be outworked and dedicated at least 30 minutes each day to asking for votes. Here’s how I used that time.

1. Take the 1:1 approach. It’s true that we tend to respond best to personal communications. So I texted all 1,000+ contacts in my phone. I started at the As and went all the way to the Zs. While this process got very monotonous and took me a week and probably 10 hours of time, it was actually kind of fun because these are all people I know. It was nice to have an excuse to reach out to them and think about them, even for a few seconds. 

For example, I reached out to flight attendants I used to fly with. Old roommates from college. Friends from high school. The husbands of friends from high school. Clients. Old neighbors. New neighbors. 

I would add in the first name to make it personal, but copy/paste the same text. Sometimes I’d stop to add a personal message too. It was fun to reconnect with people I hadn’t talked to in years. But be warned that this approach requires a lot of time, your most valuable resource as a founder/CEO.

With one more week of voting to go, I realized I could work smarter and changed my approach.

2. Go for a 1:many strategy. Next step, I emailed 100 friends of influence and asked them to share with their audience. For years I’ve been building a community of mom entrepreneurs and I know many of them have their own communities. So I made a long list of friends and business owners I trust and asked them for their help.

I specifically asked them to share with their communities, and provided them with “swipe copy” they could edit or use and a few image options to pair with it:

My friend is the founder of Comma Copywriters and it's a really cool woman-owned company. I invite you to VOTE for Comma in this business competition. It only takes about 10 seconds. 

SWIPE UP TO VOTE HERE: vote.revroad.com 

3. Get help. For ethical reasons, I would never, ever buy votes, but I realized I could buy hours of support. I hired a Social Media Outreach Assistant for the week to reach out to followers of my Instagram communities. I’d worked for years to build communities on these platforms, and now was the moment to ask for help. (See Comma Copywriters, The Mama Ladder.) 

I pre-wrote messages and had her share in my name, as my proxy. The tricky part was that I’d already personally reached out to a lot of people myself. There was no way to list out all of the people I’d already asked, and we did not want to annoy them. So I also provided her with thank you messaging, and what to do for those who already voted for Comma. (“Oops, I was going too fast. I knew you voted. Thank you so much for that!”)

4. Ask, ask, ask like a broken record. I asked everyone I talked to during the voting window. I mean everyone. When I went hiking and ran into one other hiker, I asked her to vote. She did, near the top of the mountain. When I signed up for an Airbnb place, I asked the hostess to vote for Comma. She did. When my kids’ teacher emailed me, I asked her too. When people reached out to me to volunteer in political campaigns, I asked them.  When the guy we hired to fix our roof came to inspect it, I asked him too. Whenever anyone emailed me, I asked them to vote. 

Yes, I was obsessed. But I think that’s required for a short sprint effort like this. You must be relentlessly focused and unapologetically open to asking for help. I can’t count how many times I personally asked people to vote in text, email, social media, or real life, but over the course of two weeks, it was near a thousand times. Here are places I asked people:

• Facebook groups

• Emails

• Client list

• Team challenge

• Sales team challenge - part of training to text 20 people

• Social media posts

• Blog posts

• Video, lives

5. Make it a team effort. I made specific requests for my team members, like, “Will you please text 10 family members or friends by Friday?” and this helped them be involved too. I told them I would be using the money for our upcoming retreat (true!) and that their help meant a lot to me.

6. I kept focus on what I wanted. While I had no visibility into how the voting was going (I had no idea how many votes I had or where we stacked up against others), I told myself every day: WE WILL WIN THE FAN FAVORITE. I never let any doubt creep in my mind. No room or time for that. Just stay focused on the target. I did get momentarily nervous when they sent out an email three days before and said “anyone has a shot at it.” 

But I couldn’t imagine any other founder being as obsessive about it as I was. I was absolutely determined to WIN and would not let anyone else outwork me. Nope. Not happening.

Why this drive? Part of the reason I was so determined is that I’d already hosted four entrepreneur competitions for moms in the High Five Grant for Moms since 2018. As the host, this was my chance to see how it feels for our finalists. and I wanted to give this competition a full all-out approach, holding nothing back.

Summary of tips for a voting-based business competition:

• ASK YOUR CIRCLE. Think back over your life, or at least back to high school, and write out a list of all the groups you’ve been part of. This could be church, extracurriculars, hobbies, jobs, extended family, neighbors, coworkers, etc. Reach out to them all.

• GET HELP! This is not a solo sport. Be specific: Will you please reach out to 10 people for me this week? Will you please share in your social media? 

• THANK EVERYONE. Be grateful, grateful, grateful for the support you do get. This is a time of celebration and gratitude and you can help others in your life feel they are part of your victory — you literally cannot win without their support!

What happened at the competition

During the two weeks that the voting was open, I hustled hard. I had moments of wondering if it would be worth it, especially since I didn’t have any visibility into the voting totals, but I stayed focused on my desired outcome.

At the same time, I was preparing for the pitch portion of the contest. I woke up at 4:30 a.m., gut-nervous to put finishing touches on my presentation. I only had a few minutes to tell my company story, and it’s not easy to put five years of experience into five minutes!

During the pitching portion, the vote was still open (they would announce the winner at 1 p.m.), and I was glad my assistant was still working on getting those votes while I was trying to be present and focused. I did not make it to the finals for the pitch contest, but I hung on to hope we’d still get the Fan Favorite.

Finally, it was time for the announcement of winners. “Fan Favorite” was up first. AND IT WAS COMMA! You can see what a sweet victory this was for me (on right):

When they announced my name and company and I got to accept a giant $1,000 vanity check, it made all those hours of effort worth it. I’d visualized that moment so many times, and it came true!

It turned out we had the most votes in the history of the “Fan Favorite” competition — and four times more votes than anyone else! We ended with 1,043 votes, and I’m so grateful for everyone in my life who supported me. It was one of the most rewarding days I’ve had in business.

Are business competitions worth the time and effort?

Since time is precious and limited as business owner, I recommend being selective in which competitions and grants you apply for — but do GO FOR IT! Being part of this competition did so much for me and my company. Here are a few outcomes:

• With an added boost of confidence in our growth plan, Comma has added new writers to our team.

• I was asked to speak to 300 people in for a university's Entrepreneur Lecture Series.

• We had more than a dozen inquiries from other businesses at the competition, and we're getting close to closing new clients (literal ROI for being involved).

• My business account got a $1,000 boost, and I have a giant vanity check in my home office that makes me feel like a winner every time I look at it.

• My team all shared in the win and it was a morale booster for us to be an “award-winning company.”

Good luck with your business competitions! We’d love to hear about your experience. If you’re looking for content support from an award-winning content agency (wink!), you’re welcome to contact us here.