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Three Months Later, Where are Our $5,000 Bootstrapped Contest Winners?

As you might recall, in December of 2021, our CEO, Andrew Gazdecki and Pipe founder, Harry Hurst, ran a competition for a $5,000 prize for bootstrapped founders. We heard from hundreds of you and were excited to learn about all the cool projects you’ve been working on.

However, every contest has to have winners. We selected six different businesses in their early stages of bootstrapping to take home the prize.

Now, four months have passed and our curiosity got the best of us. I asked our winners what they’d accomplished with their prize and how they were planning to expand their businesses this year.

Debs Hancock – Awhi App

1. What does your business do?

Awhi App is a peer support and wellbeing data-gathering tool. We help organizations track how their people are feeling with real-time data and help individuals practice mindfulness in their day-to-day lives.

The Awhi App helps you develop a regular practice of reflection. This includes practices like sharing daily highs and lows with friends and family. Awhi App users can also opt in to contribute their wellbeing data to analytical dashboards our clients can access for monitoring and impact reporting.

Our mission is to help create multiple layers of support around individuals. We help create this support by prompting others with data to know when to reach out to their people. We also provide organizations with an additional source of well-being data. This helps them better prove their impact and receive more resources and support.

2. What have you done/are you planning to do with your $5,000 prize?

We’re almost finished building our online self-service analytics platform. Once that’s ready to launch, we’ll use the $5,000 prize to help get the word out that this tool is ready for people to use. So far we’ve mostly brought clients onboard through word of mouth.

With all the recent reports of increased mental distress and burnout, we think the launch of this product will be very timely. Many organizations want to provide more support for their people and we’re in a position to help them take actionable steps.

3. What meaningful milestones have you achieved in the last three months?

So far, we’ve mostly worked with organizations that provide youth development programs in New Zealand. Many of the youth we work with in the country do not have mobile devices needed to participate on the Awhi App. To that end, we’ve created an embeddable widget that our partners can embed on their websites to access our app.

Inclusiveness is key to gathering a true picture of the overall well-being of these youth groups. Using the new widget, the youth they work with can share their highs and lows during the program session via tablet or PC.

4. What are you hoping to achieve by the end of this year?

We want to finish creating our self-serve analytics platform. Once it’s running, we can support more clients without needing a larger team. We can also provide our services at much more affordable rates, which we think will make us more desirable to our target clients.  

We’re also about to start a new contract with youth entrepreneurs down in the South Island of New Zealand. They’ll use the Awhi App data to help prompt reflection session discussion topics and to help program coordinators adapt their programs as needed. 

Finally, we’ll be working closely with our clinical psychologist to create short courses on our platform on how to approach and support people who aren’t coping or are facing burnout.

5. What words of advice or wisdom do you have for other bootstrapped founders?

This might sound morbid, but in my WITFAID (What in the f*** am I doing?!?!?) moments, I picture myself on my deathbed surrounded by loving family members. A grandchild asks me what I’m most proud of. I answer by saying, “I’m proud that even when faced with my biggest challenges in my darkest days, I stayed true to my values and always took the next step forward”.  

Bootstrapping is hard. But doing it ensures that your vision for the world doesn’t get hijacked for profit without purpose. Stay true to your values and you’ll always be proud of what you do.

6. What song are you listening to a lot these days?

I am currently thrashing Cloudy Day by Tones and it’s such a side-stepping-and-clapping mood-booster of a song!

Toby Green – MyCarbon

1. What does your business do?

MyCarbon is a sustainability consultancy group providing clarity in carbon. We advise businesses from the bottom of the supply chain to industry leaders on ways to calculate, reduce, and offset their carbon footprint.

2. What have you done/are you planning to do with your $5,000 prize?

We used the $5,000 prize to upgrade the MyCarbon website. We hope it will be helpful to our organic lead generation for B2B sales. We’ve recently completed the design and copy. Now we’re waiting for the developers to put the final touches together so we can get it online. 

3. What meaningful milestones have you achieved in the last three months?

Twelve months ago, we planned to have three employees in five years. We have just sent out three employment offers for junior consulting positions. It is monumental for us to reach this stage in only a year. 

4. What are you hoping to achieve by the end of this year?

By the end of the year, we want to have our five net-zero strategies validated by SBTi. SBTi is the world-leading organization for validating net-zero strategies. There is only a handful of consulting companies in the UK that have been validated by them and it would place us in a position of authority within the industry. 

5. What words of advice or wisdom do you have for other bootstrapped founders?

Don’t be too emotionally attached to your business ideas and be prepared to pivot when necessary. Books to read: The Lean Startup, Fanatical About Prospecting, Never Split the Difference, and The 12 Week Year. 

6. What song are you listening to a lot these days?

Vacation by Dirty Heads.

Josh Earle – Outlit

1. What does your business do?

Our startup, Outlit, is a mobile application to educate the next generation of fintech users.

We help customers learn about personal finance and financial products. We also help them connect with fintech apps, neo banks, credit unions, and traditional banks to get the products they need for financial independence.

2. What have you done/are you planning to do with your $5,000 prize?

The money we received from MicroAcquire has helped us pay for all of our hosting and software fees – it’s been a big help! We’ll use the rest of the money to cover costs associated with setting up our beta site.

3. What meaningful milestones have you achieved in the last three months?

Within the last few months, we’ve begun promoting our beta launch and over 350 people have signed up to use our application! We also secured an agreement with our local school board to have Outlit used in the classroom. 

4. What are you hoping to achieve by the end of this year?

By the end of the year, we hope to establish more partnerships with financial entities and schools to help more people learn about personal finance and financial products. We also hope to grow our social media presence to more effectively reach our target audience.

5. What words of advice or wisdom do you have for other bootstrapped founders?

Starting out, I thought my startup needed a lot of money to make things work. However, after I assembled a smart and dedicated team, we started creating value that money couldn’t.

I would tell other bootstrapped founders to invest more time in finding great co-founders than tracking down angels and VCs for funding. 

6. What song are you listening to a lot these days?

These days I’ve been listening to some chill, mellow music while I work. I’ve usually been listening to this Spotify playlist.

Cameron Baughn – Translate Channels

1. What does your business do?

Translate Channels is a Slack app that can automatically translate your Slack messages into over 100 languages.

2. What have you done/are you planning to do with your $5,000 prize?

After spending the last few months rebuilding the app and relaunching it with new branding and pricing, I’m finally ready to focus on finding customers!

My goal is to use the money to help with marketing and distribution – something that I failed to do in my previous startups. The extra money lets me consider marketing strategies I wouldn’t have otherwise.

3. What meaningful milestones have you achieved in the last three months?

At the end of last year, I ran into a lot of issues after acquiring this business (I wrote about them on Twitter). 

I’ve spent the last few months solving those challenges one-by-one: rebuilding the app from the ground up, designing and launching a new marketing site, getting initial feedback from early customers, and iterating our pricing model.

These aren’t the things I envisioned doing when I acquired the business and they’ve been challenging. However, it’s been rewarding to overcome those challenges and launch a product I’m proud of.

4. What are you hoping to achieve by the end of this year?

My goal this year is to increase this business’ revenue to ten times what it was when I acquired it. Its initial ARR was about $3,000 per year so I aim to get it to $30,000.

5. What words of advice or wisdom do you have for other bootstrapped founders?

After failing two startups in the last three years, I only have one thing I feel fully confident in saying: Just keep going. My first startup survived through the initial COVID craziness – including losing out on significant funding when the market turned – solely because of my stubborn refusal to give up.

I’ve heard others say this before and it’s absolutely true: “If you keep going, it doesn’t guarantee success; but if you give up, it guarantees failure.”

6. What song are you listening to a lot these days?

These days I’m listening to Who’s Laughing Now by Durry. It’s an upbeat jam about making things work even when nothing goes right. A fitting anthem for bootstrapped startup founders.

Dustin McDonald – Hyperjump

1. What does your business do?

Hyperjump is an outreach service on Twitter. We identify potential customers for you and then reach out to them individually from your account.

2. What have you done/are you planning to do with your $5,000 prize?

First, let me thank the MicroAcquire team and Pipe team for this amazing prize. It’s incredible that you awarded $30,000 to hardworking bootstrappers and continue to support the community in other ways. 

So far, I’ve spent a small amount conducting tiny experiments with the product. I plan to use the majority on marketing, automating parts that can be automated, and making it more self-service.

3. What meaningful milestones have you achieved in the last three months?

My first customer signed up for the Silver Package. Also, Hyperjump’s small Twitter presence doubled, which wasn’t a priority but is still great. 

4. What are you hoping to achieve by the end of this year?

The plan is to double the number of customers and average monthly revenue on my platform in the next year.

I am considering taking a custom tool I made for Hyperjump and offering it as a separate product to help mitigate some of Hyperjump’s platform risk. In addition, I have an NFT project that I am very excited about. Follow me on Twitter (@goodpointdustin) for updates. 

5. What words of advice or wisdom do you have for other bootstrapped founders?

A lot of the advice I see focuses on one aspect of building a startup and tries to make things black and white. “Hard work over everything else.” In reality, entrepreneurship is a balancing act. You have to balance being frugal and being willing to spend money to grow, taking action and waiting to do your research, building and marketing, working and recharging, and so on.

6. What song are you listening to a lot these days?

I actually listen to podcasts more than music nowadays.

My two favorites are “My First Million” with Sam “Hosewater” Parr and Shaan Puri and “Not Investment Advice” with Jack Butcher, Bilal Zaidi, and Trung Phan. Smart and fun bunch of people. Highly recommend.

Andrew Gazdecki
Andrew Gazdeckihttps://acquire.com
Andrew is an award-winning serial entrepreneur with three exits. He’s the founder and CEO of MicroAcquire, the world’s most founder-friendly startup marketplace, and its rebellious child, Bootstrappers, which gives voice to the entrepreneurial underdog. When not building businesses, he writes for Forbes, Entrepreneur, and now, Bootstrappers.

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