We were lucky to catch up with Tiff Willson recently and have shared our conversation below.

Hi Tiff, thanks for joining us today. Let’s kick things off with your mission – what is it and what’s the story behind why it’s your mission?

Fall of 2024, Tiff Willson, serial entrepreneur, investor, and philanthropist is launching Bold HQ. Bold HQ’s mission is to empower entrepreneurs to unleash their full potential through community and support.

Here’s the thing, you don’t have to build a business, or any bold venture, alone.

Entrepreneurs often feel like they have to do it alone. They see themselves as isolated islands, thinking they must tackle every challenge solo to the point of self sabotage. They fear being honest with their peers and tend to wear a mask that responds “my business is doing great” anytime they get asked. They worry revealing the truth that their business needs help may illustrate their doubts or incompetence. This mindset traps them, making them believe they’re alone in their struggles.

However, this does not have to be the case.

Although every entrepreneur takes a unique path, the struggles that we face aren’t unique. Entrepreneurs can also help each other out. We can listen to each other and serve as sounding boards. We can make introductions. We can tell the stories of how we solved a known tactical or technical problem. Great companies are built with the support of many, not just those on the team.

Tiff Willson has started over 20 different businesses, sold 3, and scaled 2 to millions of users and revenue. It is her goal to create a supporting network to empower entrepreneurs at www.boldhq.com

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

Today Tiff runs 3 businesses and consults 20. She is the founder, CEO of Roomhints, HiCatalyst, and Bow to the Bee. 

Using her multifaceted talents, Tiff co-founded and bootstrapped Roomhints App in 2014, to over 10 million users with little spend on marketing dollars. She further went on to sell the application in 2018 while keeping the brand.

Today Roomhints, is the #1 remodelling marketplace connecting you to sustainable design. In 2020, Tiff launched Bow to the Bee, a 100% sustainable jewelry company to support the bees.

Lastly, Tiff is a growth advisor at Catalyst, helping conscious companies to scale to millions of users and revenue.

Have you ever had to pivot?

When my cofounder and I launched Roomhints app in 2013, a week after launch, it had amassed 80,000 downloads, was featured on Apple, and we could not keep up with demand. We were so happy with the success that we thought we were invincible. But one big thing was wrong with this app – it was not making money…. and it’s burn rate/costs to keep it running per month was exponentially increasing.

During that time, the startup culture mentality was: build the product, get lots of users, then figure out how to monetize it. For example, YouTube, was a platform completely free of ads at this time and charged users no money to use it. It was building an audience. At the NY Tech event, startups pitched on stage were praised when a venture capitalist asked, “What is your business model?”

The startup would reply, “We don’t have one.” This was the norm. I will say this is in NO WAY the norm anymore.

For Roomhints, we would need to get 100s millions of users to be valuable to monetize the audience off ad revenue.

We didn’t believe in this strategy and set out to figure out how to monetize get money directly from our users.

$5 for a hint
$29 for 3 hints
$329 for full design package
$129 for the design of a room.
$99 monthly subscription to an interior designer
You name it. We tried it. We tried every iteration of the business model possible.

But nothing stuck. The more we charged, the higher the expectations and the app could not meet these expectations. The less we charged, the poorer the quality of service from the designer, and the questions were not easy to answer. “How do I furnish a living room that is 9 x 11 and has a side corner of 3 x 5?” Or I have a 5 x 5 living room and want to fit a dining table and sectional sofa.” There was no logic, and the majority of users were asking surreal questions. There was no reality to fit the furniture they wanted into their space. We would be honest and say “it is not possible with the space you have.” But that would not lead to a repeat customer. We were paid to provide them with answers.

We tried to delineate the amount that people could ask to only 200 characters and direct the questions to be one product suggestion.

Such as, “What rug can go with this living room?” But we needed the entire view of the room or space to understand this question. We needed more information. The platform needed to be able to do more.

Each failure and experiment got us closer to building Roomhints.com as it is today. Ironically, today it is the simplest form of the idea and that is what works – a premium content commerce site highlighting design professionals and featuring sustainable home remodelling products.

We’d love to hear the story of how you built up your social media audience?

I have built communities of over 1 million followers on social media and the best advice is to get into the mindset of giving. (www.instagram.com/roomhints, www.pinterest.com/roomhints)

What can this post give to my users? With Roomhints, the posts have three main themes which sit under the umbrella theme of giving/providing value
1. Quote – we feature an interior designer and give value to the designer through exposure, in addition, value to our followers from the wisdom from this quote.
2. Rooms – featuring beautiful designed spaces and rooms to give inspiration to both our professional and diy’er followers
3. Buying Guides – we do the research to find the best 5 or 6 products to choose from in select categories. This helps our followers to save time and make decisions on what products to purchase.

If you are looking for a digital marketing specialist to help grow your business and presence online, learn more at hicatalyst.com

Contact Info:

• Website: https://www.tiffw.com
• Instagram: https://www.instagram.com/tiffwillson
• Linkedin: https://www.linkedin.com/in/tiffwillson/