#107: CourseKey's Growth Equity Deal, Why You Should Practice Storytelling, A Simple Sales Hack

One vSaaS breakdown. One biz story. One 'how to'. In your inbox once a week.

Jan 13, 2025

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Alright, let’s get to it…

One Biz Story:

CourseKey’s Big Growth Equity Deal

Some of you may not know this, but my day job is as Founder & CEO of CourseKey, a vertical SaaS platform for Trade Schools.

And we shared some big news this week….

After a decade of building, I'm excited to announce a major growth equity deal with PSG.

I founded CourseKey in my college dorm room nearly 10 years ago.

We made A TON of mistakes, but we were supported by an incredible customer, employee, and investor base that worked with us through the good and the bad. I’ll be forever grateful and indebted to every one of them.

The good —

We built one of the largest software companies in our industry supporting hundreds of enterprise customers — folks like Paul Mitchell, Lincoln Tech (Nasdaq: LINC), and Legacy Education (Nasdaq: LGCY) are all powered by CourseKey’s operating system.
We’ve helped hundreds of thousands of students attend a trade school, get an incredible skill set, and attain a high paying job. Many of Americas welders, mechanics, phlebotomists, medical assistants, barbers, cosmetologists, truck drivers, etc were trained with CourseKey’s software. How cool is that?
We started with a wedge product, added a few more products, became a platform, added payments, and much much more. Much of what I write here comes from my learnings over the last decade building CourseKey. It’s a lot of things that I’ve done that have WORKED or the things I wished I would have known about or implemented sooner.
An absolutely incredible and supportive investor group and board including Steve Altman who saved the company MULTIPLE times, supported me through it all; personal challenges, professional growth, the highs and lows, you name it. The most stand up guy I've ever known both personally and professionally. Someone I look up to in every regard. Mike Stone who I learned so much from in such a short amount of time and the most sophisticated investor I've ever come across. Wayne Hu who was always there for me, his ceiling is so so high. Dennis Yang who was my CEO coach for ~5 years and made me better every day. Mark Blackwell who is a vertical SaaS guru and will do huge things. And Larry Rosenberger, who got his hands dirty and helped us build out our data & BI offering. And many others that wrote checks into a young, hungry, ambitious, kid who really didn't know much :-). THANK YOU.

The bad —

Two big headcount reductions (and one very painful one during the Q4 2024 SaaS crash that took us from nearly 100 to 40 employees)
Having our money locked up in Silicon Valley Bank during the 2023 bank run
A lawsuit the same day I got my first investor term sheet (can’t make this sh*t up)
A bunch of challenges with debt (be so so cautious of debt my friends)
Very important customers churning and very important employees and co-founders leaving
Financing term sheets that got pulled at the final hour
<30 days of runway
And a lot of other seriously near death experiences

But man, we preserved, and we made it happen.

And all this started from a little scribble on a notepad in my college dorm room.

Crazy.

So damn grateful for the ride.

Truly.

Some other incredible folks that this would have NEVER HAPPENED without — Fadee Kannah, Marc Barron, Ryan Vanshur, Luan Nguyen, Ming Zhong, S. Craig Anderson, Tina Tran, Peter Trennum, Cathy Pucher, Todd Northup, Jackson Batchelder, MA, my mom and dad, Tim Collins, Mallory & Winston, OUR INCREDIBLE TEAM, and many many more I don't have enough characters here to name :-). Thank you all from the bottom of my heart.

But the next ten years may be even more exciting than the last ten.

Earlier this year I pitched PSG on rolling up the trade school software space. They eventually bought in and three companies have come together to build the largest player in the trade school software space. I’m excited to support the achievement of this vision in any way I can.

Let this be a reminder that you can overcome anything. You just have to give it everything you’ve got over a long period of time.

Just.
Keep.
Going.

Thanks for the ride.
May the next chapter be as beautiful as the last.

Onwards,

Luke Sophinos

Link to full announcement:
https://www.businesswire.com/news/home/20250107388998/en/PSG-Announces-Strategic-Growth-Investment-in-CourseKey-to-Help-Build-a-Comprehensive-Solution-for-Career-Focused-Education

One vSaaS Breakdown:

Why You Should Become An Expert Storyteller Regardless Of Your Role

Good stories drive up company value.
Bad stories inhibit fundraising & repel talented folks.

First, to dispel any doubt—stories matter. A LOT. Good stories drive stocks up & land customers. They also create the future. The products we all use daily were once just stories about the future.

Bad stories hurt you, badly—they inhibit fundraising & repel talented employees.

Now, 2 bits of good news:

1 – You **already know** how to tell a story—and you know other people who do, too.

2 – Really good storytelling is a skill. You can learn to get better at it.

What do I mean by “you already know how to tell a story”?

Say you go on a date.
What do you do?
You trade stories.
If the stories are good enough, you get a second date.

Also: next time you get coffee, listen to the people who are gossiping.
Gossip is all about strong characters, stubborn obstacles, & suspenseful moments—those are some of the building blocks of storytelling.

Here are some of the main building blocks of a good story:

🦸 Hero
🏆 Objective (like the grail)
👹 🐲 Villain/obstacle/monster
🗡️ Weapon, potion, armor, etc… tools for overcoming obstacles

Here’s a way to map that to a business:

🦸 Hero = your customer
🏆 Objective = $$$ revenue for your customer
👹 🐲 Villain/obstacle/monster = regulations
🗡️ Weapon = your easy-to-use compliance tool & support staff

Next, here are 4 strategies I’ve been using to getting better at storytelling (I’m still learning!).

Strategy 1: Research screenwriting.

Few entrepreneurs do this, and I wasn’t exposed to it until a GREAT entrepreneur shared this secret with me.

Storytelling is a science, & screenwriters have spelled it out. There’s a great book called “Save The Cat!” (https://www.amazon.com/Save-Last-Book-Screenwriting-Youll/dp/1932907009) that shows how every great story follows a similar framework. Yours should too.

Strategy 2: Try writing something every day.

For 1 year, I wrote every day. Having to write SOMETHING each day naturally led me to write down stories about my experiences, overcoming obstacles, etc. Not all the stories were exciting, but it created awareness—now, I’m always on the hunt for a story.

Strategy 3: Get out of the building

Stories have to be shared from one human to another. You can’t be great at storytelling without constantly putting out stories you deeply believe into the world. Those who don’t *consistently* share stories with other humans can never master the art.

Strategy 4: Study the greats

There are so many examples of phenomenal storytellers who delivered great stories in the real world. I’m partial to JFK, Steve Jobs, and Nelson Mendela. Study everything about them. Study the stories they told. What did they do that resonated? How can you incorporate that into your storytelling?

Imagine what you can accomplish if you put in the work to become a great storyteller.

Acquire more customers
Retain more customers
Hire great people
Raise capital
Rally a team around a common goal
Shift human behavior

The sky's the limit!

Study and practice storytelling relentlessly.

Use it for good.

Watch the positive shift that happens.

One ‘How To’ :

Very Simple Mini Sales Hack

Want to sign multiple $50K+ customers before launching a new feature or product
Heres a SaaS sales hack to do just that…

Sit down with 10 CEO's in your space.

Show them a tool that helps them drive more revenue. Ensure it's something different than anything they have today.

If they buy-in, great, move to the next step.
If not, ask them what would help them drive more $$$

Then, ask them to 'co-design' the tool with you.

Co-design = them committing to 3 feedback meetings.
Nothing more.
Make it clear it's a SMALL commitment.

Ensure it takes <6 months to build and is applicable to the whole market you're serving (not just them).

These CEO's will feel invested in the tool and you'll likely end up with:

A new tool the whole market needs

~5 or so MM/ENT customers at launch

👊 💥 👊

Have a product or service that would be great for our audience of vertical SaaS founders/operators/investors? Reply to this email or shoot us a note at ls@lukesophinos.com