From Bootstrap to Success: 17 Lessons from My Journey in the B2B SaaS Industry

In the fast-paced world of entrepreneurship, the success stories of individuals like Alex Becker, Sam Ovens, and Russell Brunson often capture our attention and inspire us to dream big. Their remarkable achievements, from selling businesses for millions to creating billion-dollar valuations, may seem far-fetched for many of us just starting out on our own ventures. However, it’s essential to remember that every entrepreneurial journey is unique, and even small victories can pave the way for remarkable accomplishments.

While I may not be rubbing shoulders with the aforementioned titans of industry, I firmly believe that success stories come in all shapes and sizes. Last year, my B2B software company experienced a milestone that exceeded my wildest expectations: crossing the eight-figure revenue mark. What makes this achievement even more remarkable is that we accomplished it without external funding or a large team. Our success is a testament to the power of resilience, determination, and strategic decision-making in the SaaS landscape.

In this article, I want to share with you 17 invaluable lessons I’ve learned along my journey. These insights are gleaned from firsthand experience, trials, and triumphs. Whether you’re a fellow entrepreneur in the SaaS industry or simply someone eager to learn from real-life stories, I hope these lessons will provide you with inspiration, guidance, and actionable strategies to fuel your own success.

Join me as we delve into the world of B2B software, navigating challenges, seizing opportunities, and ultimately forging a path toward growth and achievement. From product development to marketing strategies, customer retention to team building, I’ll shed light on the pivotal moments and decisions that shaped our success. Together, let’s uncover the secrets to bootstrap success and embrace the immense possibilities that lie within our grasp.

Here are 17 little things we did right (& wrong).

(in no particular order)

1/ NO FREE DEMO.

When you pay, you pay attention.
Our solution solves an evergreen problem for small medium businesses in the HR space.
But the typical SaaS free demo playbook has a very long sales cycle, and it was undesirable when we were a small startup.
Instead, we charge for our software preview.
By doing that, we created a congruent sales process across all prospects.
Every prospect, close friends or not, went through the same sales cycle. The exact SAME webinar. Listened to the exact SAME pitch.
That is how we are able to refine the sales process and address the majority of the questions & objections before they even happen.
Also saw the post by many people in the industry asking about the statistics of opt-in vs AC (low ticket). In our case, we had better success gating the webinar as a low ticket. We have an average of 90% show up (over 3-4 years) compared to 40-50% show up from the free webinars we tested.

2/ NO PHYSICAL SOFTWARE MEETING.

When we first launched the software, we didn’t have a huge team. We didn’t have $10mil raised to hire expensive corporate salespeople. We didn’t have the luxury of time to go through a very long B2B sales process.
And we dreaded the traditional B2B sales presentation.
Instead, we adopted educational selling.
Except it’s gated.
Before any meeting, we send them a link to our preview.
In most cases, they will have to pay for it.
Because they went through the exact same webinar & listened to the exact same pitch, our salesperson only needs to handle a small chunk of more personal questions before they close the sales.

3/ SELL BEFORE YOU DEVELOP

This is something I’ve always advocated to my clients.
Most people spent weeks, some even months, developing an online course.
Then they found out no one wants it.
Always validate.
And the right way to validate is to make them pay.
There was the story of an influencer with over 2.6mil followers, who couldn’t even sell more than 36 pieces of merchandise of her own. And apparently, she wasn’t the only one either.

4/ ADS > OFFLINE WORKSHOP

This is how we managed to validate our MVP in 1 day, without even developing the software yet.
We did a hand-raise of “Who would like it if we built a software that does XYZ for you?” – Over 50 hands raised.
“How much would you pay?” – This is how we gauge the market price acceptance.
“Pay XXX today if you want to be the first batch of customers!” – And that’s how we validated the MVP before developing it.
We bypassed the risk of spending hundreds of thousands to develop a full-fledged B2B software only to discover that nobody wants it.

5/ PILOT CUSTOMERS.

When version 1 of the software is finally ready, we worked closely with the pilot customers.
The founders and the team onboarded them personally.
We even went on on-site visits and documented the journey as a YouTube series.

6/ LISTEN TO FEEDBACK.

During the 1st batch implementation, we listen closely to feedback and we document all of them.
Then, we categorize them and prioritize them based on how important they are.
All while making sure they align with the product vision.

7/ NEVER LISTEN TO FEEDBACK WITHOUT ASKING THE WHY 5 TIMES.

Yes, this contradicts the above statement, but let me explain why.
We need to be able to discover the root cause of “why” they are suggesting feedback
For example – a user suggested adding a delete button, but upon asking why, we realized that they just want to have the ability to edit certain things, not delete them.

8/ NEVER LISTEN TO EVERY PIECE OF FEEDBACK.

Everyone who uses software has 100 opinions about it, and they could all be good or bad.
But if you listen to every little piece of feedback and include them in your development, it may take you 10 years.
And the worst thing is you become a Frankenstein and lose your unique proposition.
It’s similar to the marketing principle of “when you try to talk to everyone, you talk to no one”.
Accept the fact that you can’t satisfy everyone.

9/ NEVER STOP INNOVATING.

Just because you’ve launched doesn’t mean the innovation stops.
When you are listening to all the problems and experiences, there may be new opportunities.
When you are digging into the “whys”, there may be new opportunities.
We are now launching version 4.0, and looking back at 1.0 it’s like amazing how far we’ve come.

10/ WEBINAR FUNNEL

Webinar is not dead. Still not.
This is our primary acquisition funnel for 4 years now.
Ads > landing page > webinar.
Because we have nailed down the offer, pricing, and target market, running paid ads is really just a math game.
Key to a killer funnel? Offer, positioning, target audience, USP.
Oh, and a very clear problem that you solve.

11/ ALWAYS QUALIFY YOUR AUDIENCE.

Most people are interested in a new software.
Not all are serious buyers.
The window-shopper, well, they can Google or wait all they want.
Serious buyers will want to pay to get their problem solved.
That is why we always take our prospects through a paid webinar as part of the key process.
How often do you opt-in to a free software demo, click “skip onboarding process”, play around with it, decide that it’s bad because it doesn’t help you, only to come back 2 years later realizing what you wanted to do achievable but you just didn’t know?
We don’t want to deal with customers like that.
Our customers, when they purchased the software, they are committed to implementing it and solving their problems. We hold them accountable. This is similar to buying a high-ticket course.

12/ ALWAYS ASK. NEVER ASSUME.

Several features got developed but shelved because we assumed our customers needed them, but they didn’t.

13/ YOU MUST HAVE A CORE FEATURE THAT YOU ARE THE BEST AT.

I remembered Alex Becker mentioned in one of his posts, that your product might not need to do everything right, but it at least needs to do THAT one thing right.
It needs to be at the level that even if they hated every other feature of your software, they still can’t leave because of THAT one thing. (can you recall at least ONE software like that?)

14/ WHAT YOU THINK IS RIGHT, MAY NOT ALWAYS BE RIGHT.

We can easily fall into the trap of assuming customers’ preferences, especially after a while. Always remember to ASK your customers.

15/ GATED SOFTWARE PREVIEW.

We charge for our preview.
That actually got more people interested.
People actually complained – “wtf? I have to pay to watch a software demo?”
But after they watched it, they either buy our software to cut short their time, or they try to implement the solution with what they learned.
We provide real value in the webinar.
Many come back 3 years later and regretted not buying sooner.

16/ POSITIONING IS IMPORTANT

We are in a very competitive space. the red ocean you’d say
But we created our own category within that red ocean and became the pioneer.
Jay Abraham or someone once said, you either be the first, or you be the best. Being the 2nd still has its advantage, but 3rd onwards and no one will remember you.

17/ WEBSITE IS IMPORTANT

The website is not dead. Never gonna.
Most SaaS (if not all) rely on websites.
The function of the website is not just to look pretty, but it is serving as the info hub for everything related to your software.
Be it the features, benefits, or success stories.
The prospects who don’t buy immediately, guess what they do? They Google you.
You want to make sure it is not just fancy but clearly structured.
After all, a good design is a design that sells.

It’s never a smooth journey. Could we have done better? Absolutely. Could we have done things differently? Perhaps. But those ups and downs are what make entrepreneurship fun. Finally, some room to breathe & to reflect on that journey.

There’s definitely more to it, may write more when I can recall them.

P.S. I still get inspired by Russell Brunson, Alex Becker, Sam Ovens, Alex Hormozi, and some others, everyday single day – how they went from marketing to developing software successfully, it’s simply amazing.