10 Powerful (Sometimes Painful) Marketing Lessons Learned as a Startup Last Year

Happy New Year.

I won’t bore you with goals or new year’s resolutions.

I’ve learned to have just one primary goal at a time to shoot for, then to set a new one once that’s achieved. That’s what works for me.

So, I hope your New Year is off to a fantastic start!

In 2018, my team and I started the year by closing out all our client accounts so we could focus 100% on selling our own products.

The result was we grew sales by 297%, or from $14,865 in 2017 to $44,108 in 2018.

After nearly 8 years in business as a sales funnel focused digital marketing agency, turning our focus to products over services quite literally made us a startup once again.

It was scary and exciting, but I had faith that this was the right next step for the business… I had faith… and nice pile of cash in the bank to finance the transition 🙂 (haha).

1,200 new customers later, I can say I’ve learned a lot—but I know both you — and I — will learn a lot more by me actually putting it down in words here.

Here are my top ten most powerful (and sometimes PAINFUL) marketing lessons learned as we began our startup journey last year…

Lesson #1 (Powerful) — A Tidal Wave of Tech is About to Crash Down On Us (And It’s Changing Everything).

I’m starting with this lesson because this is something that is, and will continue to impact your business and life (and my own), at an increasing rate.

I could easily write a definitive guide on how “Big Tech” and specifically the Artificial Intelligence (A.I.) is — and I say this without exaggeration — the single biggest existential threat to humanity — to you, to me, to everyone.

A.I. will soon replace all repetitive jobs over the next 10-15 years.

At the same time, the existential threat I refer to above is “Generalized A.I.” — something that can perform tasks that require human-level judgment, creativity, and attention to detail, and it can learn at an exponential rate…

I know what some of you are thinking.

“This is Science Fiction, Matt!” — but it’s not.

It’s real and it’s happening now. Elon Musk, Sam Harris, and the recently deceased physicist, Stephen Hawking, among others have begun to bring the threat (as well as the opportunity) to the public’s attention.

Sam Harris puts it best in a Ted talk from a few years ago (the talk is about 14 minutes but worth your time if these ideas are a new to you):

So why does this lesson make the list?

The short answer is that we’re starting to see the effects of it on our businesses now (although we probably won’t see the effects first hand for a while)…

The complete answer:

As a programmer and marketer who’s good at spotting trends before they happen, I’ve felt this shift coming for many years (before Musk and Hawking and miscellaneous VC’s jumped on the bandwagon).

About eight year ago years back I decided to do three specific things about it because I believe that much of the change will be negative (potentially disastrous) for many people.

The first thing I did was start a company.

Freedom, profit, mission — those are all great reasons to start a business, and they were mine as well.

A.I. was the fourth reason though, because it will be positive for some people, and extremely painful for the rest due to the economic shift.

Having your own business means you own an asset, and this makes you more adaptable to change than if you are working for a corporation.

Entrepreneurs will have a huge advantage over others in the coming economic shift.

The second thing I did was I started and now finished the first draft of a Sci-Fi trilogy of novels.

This lays out my hyper-realistic prediction for what sort of transformation the economy, the world, and humanity as a whole is about to go through.

I’ve literally been starting and stopping this novel for the last 15 years.

So I’m excited to share a draft of it with you coming later this year…

If you’re interested, click here to get on the waiting list.

Finally, the third thing I did was to transition our business to focus on selling products.

It will be years until A.I. completely replaces marketing agencies (50% of you just rolled your eyes at that statement, and that’s all right. Do your research and keep your eyes open…), but it will change the landscape in unexpected ways.

Growing a product business is a big challenge (see lessons below).

Still, this is my way of getting ready for that shift, because I know my skill set and knowledge can actually benefit far more people in the coming years this way.

I want AutoGrow to look out for and help entrepreneurs, marketers, and others as this shift happens.

Speaking of the tech tidal wave…

Lesson #2 (Painful) — Marketing Automation and Email ROI Is “Flattening” Out

Do you remember any of past experience checking your spam folder?

Sometimes it’s good for a laugh…

Sometimes you might check it and think:

“What? People actually click on this?”

Like that “guy” requesting you to wire him money from Nigeria based on a one-sentence email and suspicious looking link?

Yes, scam emails used to work much more often in the past.

Since Google, Yahoo, and others have gotten way better at flagging spam messages, you rarely see them.

So why do they still do it?

Because although their visibility is way down, it’s not zero.

The ROI of scamming via email has simply flattened out—plateaued.

Why am I telling you this?

Because regular email marketing is going through the same transition right now.

Gmail has it’s “promotions” tab for instance which is slowly getting smarter and more proactive at filtering marketing messages.

More and more marketers and entrepreneurs have become educated on the power of email—so more marketing emails are being sent.


For people, they have more messages to deal with and the same amount of time in a day.

Thus, on average, open and click rates are slowly dropping across the board.


At AutoGrow, I’m pretty aggressive at filtering out new email contacts who are not engaged.

Our email list could easily be 30,000 subscribers right now. Instead, we have 15,000 active people on our list.

This helps to keep response rates higher.

But I noticed that 2018 engagement rates, in spite of this, have continued to drop—ever so slowly.

After checking everything to make sure it wasn’t something with our email automation tool, I confirmed this appears to be an industry trend (see stat above)

So how do you deal with this?

Some say ads and retargeting are the answer to compensate for the drop, and that might work.

But why not just solve the problem directly so your emails still convert AND engagement is actually much, much higher than it otherwise would be?

That leads me to the solution and the next lesson…

Lesson #3 (Powerful) — Advanced Segmentation Drives Action, and Sales

As the world becomes more hyper-connected through tech, potential customers are opening themselves up to newer marketing channels (e.g. push notifications, chat-bots, text, apps) and response rates for the “old” ones are plateauing and steadily dropping (email).

As I said in the last lesson, I saw a drop in email engagement rates last year, which I learned is an ongoing trend across the industry.

You are faced with two options to solve this problem:

  • 1) Go find new marketing challenges

Some marketers suggest that dropping email rates are just proof confirmation in their almost “religious” belief in ads.

I respect and disagree with that opinion.

  • 2) The second option is to figure out how to improve engagement rates on email.

We did this in a BIG way in 2018 by re-activating and completely revamping our survey funnel.

Average engagement rates are consistently 35% across our entire list because out content is so targeted. This above average for our industry.

The concept behind a survey funnel is simple: ask your subscribers what they want and then give it to them.

By segmenting your subscribers for personalized follow-up, you keep their attention better, deliver more relevant offers, drive more sales (or leads), AND your other emails get a credibility boost because Gmail, Yahoo mail, and others “see” your emails getting read more often.

This means they are more likely to make it into the inbox for other subscribers.

The way to create an effective survey funnel is more challenging though.

It can involve a lot of questions you may not know how to answer, and many dozens of emails and automation setup.

Later this year I’m planning to launch a new product that will teach you this advanced strategy to engage your leads, and convert sales with ease by delivering more targeted email messages.

I’m tentatively calling it “Perpetual Sales Machine,” because that’s how I’ve engineered it to work.

To hear about it, you can click here to opt-in and join on the waitlist.

Speaking of “perpetual sales” I had to learn another lesson which motivated me to revamp our survey funnel in the first place…

Lesson #4 (Painful) — Cash is The Air Left In Your Startup’s Lungs. Profit is The Surface You’re Swimming Up Towards.

When I was younger, about 20 in college up at Cornell University, I used to have this mentor. He mentored me based on his own experience building a multi-million dollar tech company. I’ll just refer to him as “Brad”.

Now, mentors can teach you some really useful things.

And like anyone offering advice, they can also teach you some not so useful things.

For example here’s a NOT so useful thing Brad taught me that took some time to un-learn:

Write a business plan and then spend a majority of your time pitching to Angels and VC’s.

This was not useful because it’s better for a startup to spend time talking to customers and nailing “product-market-fit”.

In other words, when your company is young with a new product or service, you need to focus on optimizing and selling that product or service to meet the needs of your customers.

But that brings me to the super useful thing Brad drilled into my head:

Cash is King.

Running out of cash as a startup is like running out of air to breathe.

This is a painful lesson I’ve learned once before when I first started AutoGrow in 2010 and had to sell our services in order to pay rent.

It was a close call, but I focused on meeting the needs of our clients and everything turned out well.

I re-learned this lesson last year though because towards the end of the summer I decided to stop traveling and settle in New York since I had family here—and frankly, moving around from country to country was exciting for a while… But it does get to be “less fun” when you need a stable location to do work.

This instability of not having a fixed location (as well as coming to New York late in the season for finding an apartment) cost me time and focus last.

I burned through a lot of money on AirBnbs and related moving expenses as a result.

In addition, I made the mistake earlier in the year to take more drastic actions to reduce our overhead costs. For instance, I could have removed staff members and turned-off our subscriptions to key tools that were necessary to run an agency, but not for the new business model of selling products.

Speaking of products, that reminds me of another super useful lesson I learned about selling online this year…

Lesson #5 (Powerful AND Painful) — Product Range Drives Sales Volume. But Be Smart About It…

About a week before the start of 2018, I launched our swipe file product.

This was a tripwire, a resource I’ve built-up over the years. It’s a compilation of marketing campaigns and funnel asset examples that I use whenever I need inspiration. The examples come from other successful businesses.

We also had our Sales Funnel Blueprint course product which I later re-launched.

Soon after starting the year, I signed-up for SamCart, and that made it easy to take PayPal payments (many of our international customers use PayPal) and also offer one-click upsells.

As the months moved forward, I got the idea to visually layout every single possible funnel I knew of or had encountered that was worth learning from.

I thought this would be helpful to startups who needed to know about all the hidden sales mechanisms needed to create a more successful funnel, as well as what the bigger players were doing and why it worked.

I also thought marketers could use this to better communicate with their teams and pitch ideas to clients.

I was right because when we launched the Sales Funnel Diagram pack, it ended up being our highest revenue day for the entire year (it was also cool that same day was my birthday, and Avengers: Infinity War had also just come out, but I digress 🙂 )

Revenue continued to compound and stack up as the months moved forward into May and June when we relaunched the 6-Figure Sales Funnel (our most premium training).

The big lesson I learned here highlights the power of “Range” — which refers to having a range of offers and price points.

What I learned was that the more we increased our range of offers and price points, the more sales we made.

This is because, even though we get a lot of traffic for people interested in sales funnels, people have all kinds of different needs when they come into our website…

And they naturally change over time too!

So, sales volume increased the more options we had for meeting people’s specific needs and budgets,

Even though I knew this, I got distracted and it cost us $1,000’s in sales in August, September, and October…

That’s why I say this is both a powerful and painful lesson.

You see, the mistake I made was thinking we could operate more effectively as a company if we just focused on selling our most expensive product, and so I remove the other 3 products from the marketing mix, etc.

I was also distracted getting settled back in the U.S. after living in Colombia / Latin America for the last year.

When I stopped being distracted, and got focused again and turned back on our original products. As a result, sales went back up and you can see reflected in the screenshot below.

Traveling is awesome,life-changing and fun — but the lesson I learned was that I need a stable location to work AND to always build on what works (i.e. don’t “delete” the products customers are buying like hotcakes).

New Product: Speaking of product range, in the next few days I’ll be pre-launching a new product called Proven Sales Conversion Pack. If you’re interested to hear more about how it can give an instant boost to your online sales (or leads), and get a nice discount for buying early, then click here to learn more about it join the waitlist.

Lesson #6 — Content Still Beats Ads for Traffic.

I’m totally biased on this point, but let me explain.

First, I’m not saying ads can’t work for you. They can work for a lot of people (and I’m sure Google and Facebook and others are very happy that many people believe that).

If you’re a bootstrapped startup like we were at the beginning of 2018, the question of ads doesn’t really enter your mind…

Except for the one time it did.

Here’s me talking to the guy I briefly hired as our ads manager in June:

Me: Hey, do you think we can get a profitable ad campaign up and running with $X as a lifetime value for a new customer?

Him: Yes, definitely.

Me: Ok, can we do it in 30-60 days?

Him: Yes definitely.

(~45 days later what I saw were just a few new email subscribers, no new sales from the campaign, and that was it)

Me: So uh, this isn’t working. Do you know why?

Him: I don’t know.


My fault for hiring someone on the cheap.

It was also my fault because I didn’t commit the time to it that it really needed to succeed.

I say that because I think it was a big factor in the campaign’s performance. You need someone who really knows what they are doing to work with you when it comes to ads—and to obsess over the numbers if you aren’t.

I think it can still work for us down the road, but it’s going to require my focus and probably a few months of work.

That’s because the market has continuously evolved since people started crowing about Facebook and Google Ads for lead acquisition over the last decade or so.

  • 1st thing I noticed from my experience here — It’s more expensive than you think (and than other gurus tell you).
  • 2nd thing — It will take more time than you think. You need to focus on it and work with someone who knows what they are doing.
  • 3rd thing — The quality of the traffic is totally different than the quality of traffic coming in from content marketing.

A majority of our traffic today comes from search (mainly Google) and our 16,000 active subscriber email list.

These are people who are already familiar with our brand or who are searching for specific information that we can often help them with.

For these reasons, it makes much more sense for us to focus on growing these channels, because they convert better AND they bring in more and more traffic over time.

It’s like paying $10 for an ad that brings you 100 (high quality) visits in week one, but then a month later it’s bringing you 200 visits per week (and growing).

Here’s an example of an article we actually re-wrote at the end of 2017 and whose traffic has grown and grown without any additional promotion over the course of 2018.

Now, I write all the articles here on AutoGrow, with the occasional exception of a high quality guest blog article.

I do pay my team for help with editing, scheduling, and promoting our content — so content marketing is not “free”.

Also, it requires a large investment of time to do well.

Still though, the quality of the traffic from content marketing I’ve consistently found is just so much higher.

At the end of last year, I quietly launched a training called “Triple Your Traffic” where I teach you my method for growing traffic with as little as a few quality pieces of content per year.

Another benefit to content marketing is that if you stop creating content, your traffic doesn’t immediately drop.

It will drop a little bit.

I tested this at the end of 2018 and we went from over 40,000 visits per month to about 37,500 a month later, or about a 7% drop.

In 2019, I’m going to put a hard focus on growing our traffic by creating more content, more consistently.

Another reason I prefer this channel for the long term is because far fewer competitors are willing to go through the “mental pain” that it takes to write high quality, 3,000-5,000+ word articles, and guides.

So the other lesson here is “Do what others are unwilling to do.”

I explained this idea in a recent video from this past summer:


Speaking of content marketing to grow traffic, the OTHER reason I decided to test NOT writing content, was to focus on redoing our email funnel…

Because smart funnels and marketing personalization are finally taking off in 2019…

Lesson #7 (Powerful) — Personalized Content + Personalized Product Offers, FTW!

At the end of 2018, I recorded 57 videos in a period of about 50 days, from November into December.

There were 6 batches of videos.

Some of you saw me launch these to you and the rest of our Email list.

Each batch was targeting a different need.

We survey every person (or bot 😉 ) that joins our list as I mentioned above in Lesson #4.

This way, when someone opts-in we can send the most relevant content based on who they are and what they say their biggest challenge is.

All these emails and videos represented a MASSIVE overhaul to our Survey Funnel, because before this change, we were just sending a list of “top hits” from our blog.

This is part of a longer-term strategy to keep our audience engaged, but also, to grow sales conversions.

For instance, I saw that people who said “growing traffic” was their biggest challenge, are significantly less likely to buy any of our sales funnel related products.

This makes sense, right?

I can pitch you all day long on the importance of a sales funnel, but if the offer doesn’t connect with what’s important to you, you’re not going to buy.

So, my goal in 2019 is that as we grow our traffic, we’ll also be making personalized product offers to solve what startups and marketers say their biggest challenge is right now.

I’m pretty excited for this, and of course, I’ll keep you posted on the results and everything I learn if you’re a subscriber to our newsletter.

In summary, personalized content + targeted tripwires / product upsells = sales growth + a MUCH larger portion of our audience gets the help they need.

Now, it’s worth stating that creating just one great product takes a lot of effort and time…

And I have a long list of them planned for 2019.

It can feel daunting if I think about it too much.

Here’s how I plan to get it done…

Lesson #8 (Powerful) – Daily Habit = Motivation + Results. Motivation != Results (Like creating a new product, or writing a best-selling sci-fi trilogy)

Whether you have a big vision — or you just want to get something done that you know is going to require a lot of work — I’ve found that forming a daily habit is usually the best solution.

Goals can be great.

But if you think about it, a goal is something far off in the distance.

And every day, you can chase after your goal but never quite reach it.

Forming a daily habit, or work system, is better.

This is more “naturally addictive” because our brains release dopamine (which makes us happy and helps us learn) whenever we complete a task.

So, you want to have what I like to call a “Daily Engine”, like I do.

It helps you finish each day with a sense of accomplishment.

My Daily Engine looks like this (it’s very simple):

  1. Affirmation (for instance, I write my primary short-term goal that I am focused on right now 9X). I’m not into the Law of Attraction or any of that per se, BUT, I like to do it because writing my affirmation is an easy to complete task to start the day (I get a boost), and it reminds me of what my end goal is.
  2. I journal for 15 minutes (whatever is on my mind, whatever I’m excited about, whatever problem I’m trying to solve, etc. It clears my mind and leaves me feeling fresh and unburdened.)
  3. I complete my “Kill Task” for the day. Your kill task is your top productivity task. You will beg, borrow, steal, and KILL to get this task done (not literally of course). The idea is not to end your day without completing your kill task, because when you do that, you’ve taken one solid step towards accomplishing your primary goal!
  4. Anything you complete outside of this is a bonus.

When I was creating our Sales Funnel Diagram Pack product in May and April of last year for instance, my daily kill task would be to create 2-3 funnel diagrams per day.

After I had all 28 completed, my daily kill task shifted to recording strategy walk-thru videos to go with each.

So I’d do 2-3 per day of those.

This work over time added up to a completed, original product that our hundreds of customers have bought love.

I’m doing something similar for our upcoming new product, Proven Sales Conversion Pack (this one is a bit more comprehensive and will take longer to make, but the value to our customers in the form of growing their sales is going to be awesome, I can’t wait to hear the feedback…click here if you want to learn more about itget on the waitlist.

I’d said this was a powerful lesson, but it was also a slightly painful one.

Whenever I forgot it, it was easy to get overwhelmed by the amount of work I felt I “had” to get done…

I’d forget about the daily system, and instead just focused on various goals, and how far I felt I was from achieving them (not good).

Learn from what I’m telling you here: focus on your system, not goals.

Because you’re always “failing” until the moment you reach your goal.

With a daily system, you “win” and make progress every day.

It’s sort of like a game.

This is the same way I wrote the complete first draft of my (editing now) Sci-Fi trilogy back in 2017.

I woke up every day, and wrote 1,000 words for it.

These words added up to many pages, until I had three completed novels.

Lesson #9 — Structural changes (e.g. new product, new funnel) beats optimization (AB testing, “mickey mouse” stuff). Both Combined at the Right Time Beat Everything…

This is getting a bit long so I’m going to be brief and to the point with these last two lessons.

What I learned in 2018 is that, when you’re just getting started and you want to grow sales, focus on BIG changes.

Like setting up a new sales funnel.

Or launching a new product.

Or creating and launching a new lead magnet.

These changes are MEANINGFUL and difficult.

But that’s a good thing, because they are more likely to get people’s attention (and because they provide more value to your audience).

Too many entrepreneurs (and marketers) can get caught up with the small “mickey mouse” stuff… like:

  • A/B Testing (when you don’t have enough traffic to justify it).
  • Getting your website design just “perfect” (when you don’t know the market or if they’ll buy).

When you are a bootstrapped startup, as most are, you need to focus on what matters.

That’s why Structural Changes in your marketing always beat optimization.

If you’re too busy optimizing, you won’t launch, and you’ll stop yourself from SELLING — you need to give your startup “air” like how I put it in the above lesson.

Once you get some traction, once you GROW your traffic, THEN (maybe) it will make sense to start optimizing.

Before that though, you are holding yourself back.

Lesson #10 — Forget The Hype. Compete with Yourself!

I’m like a sponge.

I roam around the internet and go down all kinds of “rabbit holes” to learn around random things, or to see what other businesses / entrepreneurs / marketers are doing.

I used to be subscribed to 100+ newsletters, which helped me learn for a while…

But after this year, I decided to unsubscribe from almost all of them (except ours of course, and a few other quality ones)…



If I hear how easy it is to make $100,000, $200,000, $1,000,000+ again I’m going to puke (and I know I’m not alone on that, you’d probably agree with me).

Growing a startup from scratch is work, no doubt about it.

I’ve been sharing our monthly growth reports with you, and if you’ve seen them, or you’re a startup right now yourself, you know it is NOT easy.

You have to work at it, and you have to take action, everyday.

Yes, there are proven systems, tricks, tools, and all kinds of cool stuff that make the journey easier, faster, more profitable (that’s what our products are created to help you with!).

But to succeed, you have to take action, and you have to constantly learn, and apply what you’re learning.

“Passive revenue” is (mostly) a myth.

So I say, compete with yourself, forget the gurus, forget all the “hype” that’s always floating around like if you’re not instantly earning $100K or $1MM+ you’re failing.

Forget all that!…

Take a deep breath…

And focus on what really matters:

  • your customers,
  • your leads,
  • and making “one-foot-in-front-of-the-other” daily progress.

Conclusion (and Worthy Mentions)

There are a few other lessons I have learned and can expand upon in future articles.

Just leave a comment if one specifically catches your eye.

Here are the worthy mentions that didn’t make the top ten lessons list above:

  • You can “manufacture” social proof.
  • Use the daily news as a marketing opportunity.
  • Positioning thru framing (marketing strategy).
  • Seasonality has a huge impact on sales.
  • Creating original products gives you a competitive advantage.
  • Recurring revenue is so sweet and makes business more predictable. One-time product sales are not as sweet. Sometimes, it can feel like an uphill battle every month.
  • Your mind is a “Chinese Room”. You are always a victim of your environment. Shape your work environment to optimize your productivity.
  • When you’re a startup, think of your customers as your investors. Show them as much love as possible.
  • Low-priced products does not mean low profit, especially over the course of a year.

That’s a wrap for now.

A bunch of what I learned is now going into our new, upcoming product, Proven Sales Conversion Pack.

We’ll be opening it up for pre-orders soon, so join the list if you want to learn more about it hear more about it, and pre-order now an early-bird discount (in exchange for your feedback).

I’m only planning on making 15 spots available for it to start…

Which of my 10 lessons learned above most connected with you?

How will you learn and apply what I taught you about here?

Leave a comment and let me know.

Keep hustlin’, stay focused,

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