Our Ugly Startup Story - How we started our business (It is not glamorous - so be ready)

171: Our Ugly Startup Story – How we started our business (It is not glamorous – so be ready) [Podcast]

by | Apr 14, 2020 | 0 comments

Our ugly startup story is something I have told many times – usually when I am speaking at an event. But, since I recorded the 9 steps to generate $30,000 per year, I have been talking to many of you about how you can start something. A lot of misconceptions and overcomplicated ideas out there. I wanted to open up and show you what a startup looks like for real (not the idealized things you see in Facebook Ads). So today I share our ugly startup story which will include lessons learned and how we might do it differently today.

Our Ugly Startup Story – The AskDrCallahan Startup Story

First, we were led to homeschooling our two daughters. The story was a three-year path from “we have never heard of homeschooling” to starting up. Get more details here. About us.

The PAIN.  The path into the business came from learning about PAIN. Friends, who were homeschooling and finding their kids also going into high school, were afraid of math. They simply could not teach high school math (their words – not ours.) This was the pain – they needed solutions. Knowing Lea and I are both engineers – they wondered how we might handle this problem. Pain is an important word here – pain is what makes people seek solutions and spend money. I am not talking about physical pain – we are talking about frustration or desire for something one does not have. Marketing pain.

We were almost talked into starting a business. It was worded as “Can our son join in with you teaching your daughter – we will pay you. So we started to help. Then it grew into our pain. 

I will skip the details here because some of them are in our published AskDrCallahan story, About Us, but after 3 years of this, we were teaching a massive amount of courses in our basement.

We were at a crossroads. Lea wanted to move us to a new plan and put the courses on DVD and sell them to friends or open a school. Since I always like to have 3 options to make a decision – I came up with a third – do nothing. Quit. I liked the sound of that option.

The Opportunity Analysis

To determine if going for a real business model with homeschool math, we needed to do an opportunity analysis. This is a quick way to determine if there is enough money to be made. The details of this initial analysis can be found on Podcast 87: How to Do an Opportunity Analysis. The key was that the numbers looked interesting enough to move forward.  This process took about 30-60 minutes!


Once you know the idea is a go  – you just have to start. We decided on the right product to start with – the one we already had done a few times – Algebra 2 with Trig. The notes were ready, we just needed to get started and put it on the market.

Stupid Steps In

Call it stupid, distracted, perfectionist, etc., does not matter. This is the place where we start to overcomplicate things. We always do – and so do you. I know, I coach startups and see it EVERY SINGLE TIME. My stupid showed up with me wanting to create a video studio, buy the best equipment, and – well I will not go into more details, but you get the idea. Stupid and distracted. My wife (who as it turns out represents the customer base – more on that in an upcoming podcast) told me “Homeschool moms do not want fancy, they want the problem solved. It does not have to be pretty or packaged well – it has to solve the problem!” This is a great time to heed the quote,

“If You’re Not Embarrassed By The First Version Of Your Product, You’ve Launched Too Late”  – Reid Hoffman, founder of LinkedIn (Billionaire)

So I took a whiteboard, a camera, and started teaching the course just like we did at the university. (OK  – I do not teach math at the university – but you get the idea.)

With our daughter doing the video editing (something she had never done), we had a product in a few weeks.

Tell the World

This is the MOST IMPORTANT PART OF BUSINESS – MARKETING. If you have a great product and nobody knows it, then who cares.

We started with a website. Since I am not a great designer, I did some R&D (robbed and duplicated.) I found a page I liked, copied it, added our words and photos, and off we went. Below is the first homepage. Not bad – and served us many years.



If I was starting today, I would either use Shopify (the easiest option and will cost around $30/month) or WordPress off a SiteGround web hosting service (an option that takes a little more skill and will cost about $100-200 per year. )

Then we placed ads in a few homeschool magazines. These worked enough to generate traffic. Today, I would skip the magazine and do Facebook Ads instead.

We also went to a few conferences for homeschoolers. We decided not to do many of these because we found it was not a fit for our business – and frankly, just not that much fun for me.

The First Order Comes In

On our website, we packaged our DVDs, the book, and the solution manual. The book and solution manual were bought used from Amazon. The first order for the package was about $300.

OK, ready for weird? When I saw the order come in on my phone, we were out of town. I groaned to Lea – “Oh no, someone just bought the course. Now we have to burn a set of DVDs and actually ship it.” Yes – that sounds sick. Lea told me “Someone just sent you money and you are complaining about it?”

Truth is, I complained about the first many orders. They all meant work that I did not like to do. But we did it. Even though the details were a pain, I enjoyed helping the customers get what they needed.

And you want to talk about pretty packaging? We had the best. Below is what the package looked like.

These were DVDs we bought in bulk at Sams, printed the label on an inkjet printer that had a DVD printing attachment, and packaged them in DVD cases bought by the 100 at Sams, and then wrapped in painters tape to keep them together for shipping. Pretty huh? I kept waiting for Apple to call me about becoming a package designer for them!

The Key To Growth – Customers Who Talked

I never really got past the packaging and shipping issue. I am not a detailed person – and this was a detail. But over time we found better solutions and had many growing pains and epiphanies.

The key was talking to customers. People are funny, it is hard to get opinions out of people about the right products and services. But once they buy from you, they really start talking.

Much of our growth came from listening to customers. What they needed. What they liked. What they struggled with. Each email, phone call, Facebook comment, etc yielded new information about where we were to go next.

Even today, customers are still telling us the path to take. We no longer advertise (we should – but just do not at this time.)

Why Am I Sharing Our Ugly Startup Story?

Where have we gone from this messy packaging and print? – more on that in an upcoming podcast.  But the reason I share is to encourage YOU.

You too will struggle. Your business may be something you love – but it is messy in the middle. Always. It might be a fun mess – but always a mess. That is OK!

I want you to see the path forward for your idea. It might be right in front of you. It might be begging you to be in business.

Your Biggest Challenge Will Be ……

You. You are going to be the biggest challenge. Thinking through business ideas, next steps, and staying out of the weeds is a constant battle for startups. What worked for us, and what works for my coaching clients, is to get a clear path to success. To do that, you have to get the mindset straight – which is not trivial.

  • Do you feel overwhelmed with your startup – not sure what to do first?
  • Do you feel like you have nothing to sell?
  • Do you think you are not qualified?
  • Do you think you need one more degree, one more training class, etc before you start?
  • Do you think that no one needs what you do because it is obvious and simple?

Hopefully, you can tell from our ugly startup story that we had some of these same issues. Not all – and neither will you.  But your ugly startup will entail a lot of your personal hangups.

You are normal. Get unstuck. This is how I help. I help people just like you to get unstuck so they can grow their income from a business or a new job – sometimes both.

Let me help you for FREE. Get on my calendar for a free 30-45 minute discovery call – where we help you develop a roadmap to success. No obligation – this is just me helping you. 

What am I working on now? 

Moving past our ugly startup story, many of you have asked what we are now working on. So here is a list of activities we are adding to our ugly startup story.

  • Help people like you see Ideas – “I love cooking, what to try?” 
  • Fiverr / Udemy / Facebook Live / Youtube Posting
  • One thing at a time  – otherwise overwhelm
  • Avoid the trap of trying to look like the other guy. Someone who has been doing something for years is a trap to you. 
  • My brother used to tell me – “There is always a bigger fish story.” There is ALWAYS someone with a bigger team, bigger budget, bigger audience.


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Dale Callahan

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