10 Lessons Helping Entrepreneurs From Idea to Scale

At the end of December, I often reflect on what happened throughout the year. I like to remember the good, grow from the bad, and avoid the ugly lessons.

I thought I’d share 10 lessons from my experience helping entrepreneurs go from idea to scale with you.

Lesson 1: Positioning and messaging can make or breaks startups. Especially early-stage companies.

Language shapes reality.

When I began learning about marketing, I thought branding was a bunch of “squishy, ephemeral, fluffy stuff” which everyone needed but no one should care about it. You know, things like your logo, design, and colors. You need ‘em, but very few care about them.

It was foreign to me why Facebook spent $200,000 to go from “thefacebook.com” to Facebook.com. (Source) Not to mention how confused I was when later learning they spent $8.5 million to get FB.com. (Source)

Fast forward to the present.

I’ve seen content marketers make a fuss over word tense, preferring active to passive verbs.
I’ve seen copywriters making six-figure incomes labor over a single word.
And I’ve seen a web hosting client of mine double their annualized revenue in six months with a 10-word unique selling proposition (USP).

If you’re familiar with my content, you know I’m a huge advocate of you talking to your customers. You can complete 70% (or more) of your business model by asking your customers the right questions.

The language you use has such a strong pull, it will change your priorities and your focus.

Lesson 2: Successful entrepreneurs know how to focus.

Are you curious what the 10-word USP that doubled a web hosting startup’s annualized revenue? Here it is:

Get 15% or faster web hosting by switching to Decibite, guaranteed.

No longer was Decibite struggling to rise above the noise from 100’s (if not 1,000’s) of other web host companies Plus, the language provided Decibite the focus they needed.

There’s less discussion now what features they need to build to keep up with the web hosting Jones’s. Instead, it comes down to a simple question, “Will this help our clients get faster web hosting?”

Entrepreneurs who win focus on what’s happening on the playing field (creating value for customers), not the current scoreboard (revenue).

Of course, your business needs money to survive. Which takes us to the next lesson...

Lesson 3: You can’t guarantee a future opportunity without money in your hand.

The possibility of future opportunities can be exciting. And it’s great to have a feeling of success. But until you have someone’s money in your bank account, you should not make any major decisions until you do.

A customer is not your customer until you have money in your hand. An investor is not your investor until you have money in your hand. And an acquisition offer is not an acquisition until you have money in your hand.

It doesn’t matter if an enterprise client wines-and-dines you, drafts papers with their lawyers, or does anything else that looks like a positive commitment. 

As Yogi Berra would say, “It ain't over till it's over.”

Lesson 4: Never stop learning from everything which fascinates you.

When I first began learning about the world of internet marketing, I read anything and everything that I found interesting.

Some topics I applied right away, like content marketing. Other topics I’ve started applying in my work this last year. But since I had three years of intermittent research, I wasn’t starting from scratch. I knew the principles to focus on and who had expertise on what niche topics.

There are even marketing topics that while I have not applied myself has inspired other successful campaigns. 

I’ve been studying network effects for a year-and-a-half. As of this writing, I have done only a little marketing for network effect businesses. But I took a principle I learned from that research to create 90 bottom-of-the-funnel landing pages in a month to scale Decibite's SEO. This was a huge contributor to Decibite's product marketing strategy to 2.3x their annual recurring revenue in six months.

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This is why I read anything and everything that catches my attention.

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Related Article: The best landing page builder I use to scale SEO campaigns

Lesson 5: Most successful startups built an audience first.

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Earlier this year I had the privilege to interview 10 SaaS founders to learn what they did to get their first 1,000 customers. 

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One fascinating insight I learned is that these successful founders either:

1. Turned a service they've done into a software as a service.
2. Experienced a personal problem, then tapped their existing network of people with that exact problem.

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Consider the 10 people I interviewed:

1. Steli Efti: Close.com started as an outsourced sales team. They then created Close as an internal CRM tool because they did not find other tools adequate. They later changed the tool once other salesmen saw their product and wanted it.
2. Hiten Shah: Shah first built up a network through Product Hunt and several other successful companies. His startup FYI got many of its first customers launching on Product Hunt. 
3. Spencer Fry: Fry’s parents are professors and he knew someone making $500 as a GMAT tutor. This first customer persona wasn’t super successful. But Fry also previously had a project in design. These creators were a much better persona, which led to the success of Podia.
4. Jordan Gal: Gal and his brothers had an eCommerce store. He knew the value of having a better checkout cart, and the solution he currently had wasn’t helpful. So he launched CartHook using his network of other eCommerce store owners.
5. Jay Myers: Similar to Gal, Myers ran his dad's eCommerce store before starting Bold Commerce. They now have a suite of eCommerce tools, many of which came from his experience running his dad’s store.
6. Laura Roeder: Roeder offered social media marketing (SMM) and had online courses on SMM before starting MeetEdgar. Her blog email list, clients, and course customers became the initial test group and launch platform for her first several customers.
7. Sam Saltis: Saltis ran an agency creating eCommerce websites. He then created an eCommerce content management system, which later became Core dna.
8. Michael Higgins: Higgins ran a large business with 1,630 employees before realizing the challenges of business accounting. He then used his employees to start and beta-test PurchaseControl.
9. Aki Balogh: Balogh did content marketing at a startup and VC firm. This allowed him to see first-hand the challenges of creating relevant content. These connections became the first people he tested MarketMuse with.
10. Chris Gimmer: Gimmer had a WordPress theme marketplace and used content marketing to get new customers. As he blogged, he noticed how difficult it was to create photos. He wrote a viral article on where to find free stock photos, used that audience to build a free stock photo site to get leads, then used the article and free stock photo site to launch Snappa.

I get 10 is a small sample size. But I’ve found this pattern when talking to many other clients, prospective clients, and other successful founders too.

Mark Zuckerberg started with his fellow Harvard students. Reid Hoffman tapped into his network from Paypal to build LinkedIn. Andy Rachleff began Wealthfront from his connections at Facebook and LinkedIn.

Is this always true? Maybe, maybe not. However, it makes sense that people who know you will be the easiest people to get new customers.

If you want to start a successful startup, it will be easier to solve a problem with people who already know, like, and trust you.

Lesson 6: Too often entrepreneurs focus on marketing strategy first and business strategy second.

The most common questions I hear from entrepreneurs relate to their marketing strategy:

1. How do I find my first scalable marketing channel to get my first 1,000 customers?
2. How do I find out how much my customers will pay for my product? 
3. How do I create a USP to differentiate my product from my competitors?

It makes sense marketing strategy questions are more common to think about first because entrepreneurs feel these pains first.

Unfortunately, entrepreneurs aren’t aware that they should dig deeper into more important questions related to their business strategy that will inform their marketing strategy.

1. What are the five stages of customer psychology I need to create content to educate customers on our website who come from different marketing channels?
2. What should I think about when creating my pricing strategy?
3. How do I create a voice of the customer program to talk to customers and find out what points of differentiation are important to create my USP?

Both types of questions are important. However, your business strategy will inform your marketing strategy, even if you have no formal strategy in place.

Lesson 7: People love to help if you approach them right.

You’ve heard me say a few times now that you should talk to your customers. If the goal of a business is to serve customers at a profit, then it makes sense that customer needs should direct your business strategy.

A concern which stops entrepreneurs from talking to customers goes something like this:

“I get talking to customers is valuable. But are they really going to hop on a call? They’re busy people and their time is valuable.”

There is some legitimacy to this concern.

Each of us only has 24 hours in a day. People rarely take the time for drawn-out meetings from random strangers.

Here’s the thing:

1. You are not a random stranger to your customer. You solved a problem they have and many are grateful you did so.
2. You add value to your customers by learning how to better serve them. After some customer interviews, people have asked me for my notes because “This was more beneficial to me than talking to a therapist.”
3. Most people love to help other people out.

Sure, not everyone will be available to help. If you follow my email outreach program, you should expect 20-40% of customers to reply to your email.

Doing five customer interviews is a good starting point. You’ll likely get great insights in three interviews. (But I suggest five to give you some practice and you may interview some customers who don’t provide many details). I recommend 15-20 customer interviews once you’re convinced of the value.

Lesson 8: Challenge and test your assumptions.

On Twitter the other day, a PPC marketer I know and respect posted this:

His team has made money for companies like Nike, Nickelodeon, Duluth Trading Co, Aerosmith, Infusionsoft, Kaiser Permanente, Allen Edmonds, and Lane Bryant. I say this because this isn’t some random marketer on the Internet making a complaint.

Cold emails are notoriously bad. Go check your spam folder if you’re curious how many bad pitches you’ve missed.

Yet I plan to double down on cold emails this next year. Sure, I use cold email more for marketing than sales purposes. But it still works.

Don’t take what someone says on social media or their blog at face value, including what I’m writing here. (Especially if they only have 280 characters to do so). 

Yes, everything I write comes as a result of my experience. I don’t write articles for the sake of ranking content in search engines (though that’s a part of my content strategy). 

But you need to test what I write for yourself to truly see if what I say applies to your business.

Lesson 9: Planting seeds today creates new opportunities tomorrow.

Steve Jobs once said, “You can’t connect the dots looking forward; you can only connect them looking backward.”

I advise clients to take reasonable requests which takes them five minutes or less to do.

Does someone ask you for feedback on their landing page relevant to your expertise? Give them a quick five-minute analysis.

Did you find an article you particularly enjoy? Sharing it with a few friends on Facebook or Twitter.

Is a friend asking you to test their new software? Give them a couple of minutes to be a beta tester.

Yes, that specific way you helped them may not lead to their success for that project. But they won’t forget how you made them feel in that moment.

Lesson 10: Don’t be the smartest person in the room. But don’t be jealous of smarter people either.

I’m active in six business and marketing communities. Most are private, invite-only groups (but Reddit’s startup Discord is an open community worth checking out).

In one group, I’m constantly impressed by the next-level thinking these marketers are considering, testing, and doing. 

More often than not, this causes me to stretch my thinking. However, I’ll admit from time-to-time this also causes me to become jealous of these marketers. 

For example, one of these marketers started a couple of years after I did in a more junior position. He’s now the head of growth at a multi-million dollar eCommerce brand and co-founder of a growing startup. It’s easy for me to look at his success and tell myself I should be where he is today.

The same can be true for you. It’s wise to be around and learn from entrepreneurs who are smarter than you. But be careful you don’t become jealous, which only leads to ruin.

I’m thankful you’ve taken the time to learn from me. This could be your first time reading what I’ve learned (hi!) or you’ve read my content for years. I hope my articles continue to be valuable to you to help you become a smarter entrepreneur, marketer, and human being.

Here’s to a fantastic new year.