Entrepreneurial Experts Weigh In: What You Need to Know When Starting Your Business

Every entrepreneur who has been running their own business for a while wishes he or she knew more when they were just starting out. Each of us would love the opportunity to speak with our younger self and give advice that would make the journey easier, less painful, and speed up the path to success.

With flyte new media approaching our twenty-fifth year in business, I’ve got enough advice for my younger self to fill a book…or even a Netflix mini-series. Maybe that was the prompt for reaching out to many of the entrepreneurs and business experts I’ve met over the years and find out what they’d say to themselves if they had a time machine handy. 

Below, I’ve collected their sage advice: the things they know now that they wish they knew way back when. What’s interesting is that as I reviewed the advice from this curated list of entrepreneurs, I noticed a few recurring themes:

Mindset Is Key to Entrepreneurial Success

The most popular advice was around mindset. Too many business founders suffer from imposter syndrome, believing themselves unworthy or too inexperienced to succeed. They looked at others who had been in business for years and compared themselves to these successful business people. This caused them to undercharge and undervalue their own work.

Of course you’re not going to have all the answers when you first start out–the impetus behind this post!–but chances are you are experienced in certain specific areas where you can help others and make a name for yourself.

Business Owners Don’t Go It Alone

Another recurring theme was that founders wish they had made their first hires earlier, even before they were ready. There’s a myth around the self-made man or woman, but that’s all it is: a myth.

The idea of hiring people before you’re comfortable with the idea is something that definitely resonates with me. I waited way too long to hire my first employee, my first contractor, and my first consultant. 

I still tend to be a little hesitant when it comes to adding to flyte’s growing workforce, but I’m much more likely to hire based on forecasted growth rather than waiting until we’re all drowning in work.

Two of our experts gave the exact same advice, specifically suggesting that you hire a bookkeeper as soon as you can afford one. I’d add to that and suggest that you get all the financial help you can afford: bookkeeper, accountant, fractional CFO…whatever it takes. 

Create Systems for Growth

Many business owners wish they had created better systems earlier on, and again, I count myself among that group. When I think back to how I tracked my time (I didn’t) and my projects (sticky notes on a wall) when I first started, I’m amazed I’m still in business!

Many of our business owners found that when they created systems for planning, implementing, and tracking their projects and their results, their businesses boomed. 

No matter how small you are, or how creative your work, invest in systems that will allow you to plan, grow, and track that growth.

Expert Advice on Starting and Growing Your Business

Expert Quote - Do Things That Don't Scale

You need to do things that DON'T scale. For those just starting out, time is your biggest advantage. Those who have already achieved success lack TIME. TIME is your biggest and most valuable asset. USE IT to do things that don't scale. It will give you the knowledge to do things that DO scale down the line.

John Lee Dumas
Entrepreneurs On Fire

Tamsen Webster

There are so many things I wish I knew when I first started out. But I think the biggest one is that luck plays a much larger role in your life than you would like, so learn to live with it. And here’s what I mean. I am someone who loves to make plans and anticipate things, and I had all sorts of expectations about how things were supposed to go. And I know that people say you can make your own luck, but you know what, you can't make your own luck around everything. You cannot unmake a merger happen. You can’t unmake an awesome boss decide to retire. You can't unmake some major life event
happen in the life of one of your colleagues or teammates. I mean, heck you can’t even unmake a global pandemic. The only thing you can do is anticipate as much as you can. When something unexpected does happen, assess the situation and check in. How does this affect what I was thinking about doing? Is this a new opportunity to go somewhere else, to do something different? Or is this a time to dig in further with what I know I want and need to do? And then adapt, adjust, act accordingly? But luck is a friend, but it is a very fickle friend. And that’s what I wish I knew when I was first starting out.

Expert Quote - Build Your Email List

I wish I knew the importance of building an email list (and regularly sending awesome content to my email subscribers). This one thing has made the biggest difference for my business over the long-term.

Brian Dean
Exploding Topics

Expert Quote - Hire Others Early in Your Career

Do what you do best and hire others to do the rest. I wish I had hired an assistant - and then a team - much earlier in my career. I believe that is the only way to truly scale your business. Even if it’s hiring only 1 or 2 extraordinary people to support you.

Viveka von Rosen

John Jantsch
Duct tape Marketing

Hey flyte nation folks, this is John Jantsch with Duct Tape Marketing. And a couple things that I wish I knew when I was just getting started. I'm going to give you two, because they’re kind of related.

The first one is, there is a real correlation between price and value, or perceived value. And the funny thing about it is, the more you charge, the more the value is perceived to be greater. So the lesson in that is, you’re probably undercharging. If you sell a service and a lot of the thinking is, “Oh, I want people to buy from me, especially when I’m first getting started, so I need to charge a cheap price.” Well the unfortunate thing is, you are literally scaring away people who actually want value, who are actually very serious about investing in what it is that you do. Because they feel like, well, if you’re only charging that, what could it be worth? So that’s number one.

And the second one is, you need buyers. It’s so much easier to sell more to existing customers. So create products and services that create buyers, then you can sell that high-priced, high-ticket item to them.

So there’s your two-for-one, things I wish I knew when I was just getting started. School of hard knocks taught me, and it’s certainly a lesson that I hope you take right away.

Expert Quote - Create Routines (Even if You’re a “Creative”)

Looking back, I wish I knew that every time I said the phrase "I don't like routines, I'm too creative and spontaneous" I was pushing my success back by 6 months. Each time I refine my daily habits I see a huge jump in my success...emotionally, physically, and financially.

Dana Malstaff
Boss Mom

Expert Quote - Publish Deeper Content

Go deeper sooner. If I had a time machine, I go back and start publishing deep, visual how-to content and original much earlier …instead of the weird SEO poetry and zombie-themed posts I was writing back then.

Andy Crestodina
Orbit Media

Expert Quote - Avoid the Emotional Rollercoaster

When I started out, I tended to be an emotional roller coaster, with ups and downs tied to whatever was happening in my career at the time. A few years into owning my own business, my Dad gave me some of the best advice I’ve ever received, and I dearly wish he would have told me sooner: “Things are never going as good as you think they is. And they’ll never go as bad as you think they might.” This really helped me keep a more even disposition in business and in life!

Jay Baer
Convince & Convert

Expert Quote - Be Strategic and Work Your Strategy

I wish I had started with more strategy in mind. When I started, I was just doing all the things with no real goal. Until I got strategic, I wasted a lot of time that could have been much more efficient in building my brand.

Jenn Herman
Jenn's Trends

Expert Quote - Invest in Paid Media

I wish I knew that paid media would play such an enormous role in everything I did, even though I am more of an owned and earned content guy. Had I understood more about media planning and buying at the start of my career, I probably would be rich and retired by now.

Jason Falls

Neal Schaffer


What I wish I knew before, was that everything in digital marketing takes time. But it is the time spent and the consistency in the time spent that yields results. You know, I began a lot of different types of content creation initiatives. I launched my first blog back in 2008. And while I continued to blog in 2009, 2010, there was a time where I just left my foot off the gas pedal. And I did the same with my podcast. I launched it in 2013 and went strong for a year or two, and then once again, I paused it for a while. Same with my email list and YouTube videos as well, I can say the same thing.

So if I had been consistent and really stuck with everything that I did early on and just continue to do it at a regular pace, I think it would have led to much more authority in the search engines, much more authority in the public. And with that comes the additional business and thought leadership that I think I might’ve been able to yield. Not to say I’m not happy with how things have turned out, but hey, there’s always room for improvement. I’m a Kaizen type of guy, and these are things that I hope you will learn from me, to help you and your business's digital marketing in the future.

Expert Quote - Perfection is the Enemy of Success

Early on when starting out with Facebook Ads, I spent too much time making the perfect ad with the perfect ad copy. What I know now is that the volume of ads and variety of ads is more powerful than the perfectionism of one ad that the algorithm may or may not like in the end.

Amanda Robinson
The Digital Gal

Expert Quote - Mindset Trumps Everything

That mindset is everything! You can have the best tools and strategies in the world, however, they don’t matter if you are too scared or you're letting something hold you back! Working on my mindset has been the single biggest game-changer in my business.

Teresa Heath-Wareing

Expert Quote - Compare and Despair

When I first got into the internet and business world, I saw people online and often thought, "Wow, I could never do that (or be that)." But the more I got to know these people, the more I realized they were all screwed up. They were all imperfect. They all had their struggles. In other words, they were just like me. And somehow, once I realized that, I never looked back.

Marcus Sheriden

Expert Quote - There Are No Shortcuts

You've got to roll up your sleeves, there are no shortcuts! Competency in anything (marketing, leadership, Facebook ads etc.) comes with hard work, curiosity, dedication to the task at hand, and time.

Dorien Morin-van Dam
More in Media

Expert Quote - Track Results and Be Specific

I wish I had done a better job of keeping track of all the campaigns and clients I worked with and the results we generated together. It's not enough to tell potential clients (or even employers) that "I increased leads and decreased costs." You need numbers, specifics, impacts. Getting customer tutorials is great, too, but also make sure you are keeping a record of concrete results. Future you will thank you.

Alisa Meredith

Expert Quote - Know Thyself

As a consultant, when I was first starting out, I wish I had known there is no one 'right way' to deliver work. It took me a long time to figure out that I'm best suited for video/verbal delivery (vs. big long typed documents). I tried to make myself do documents for a long time but I was unproductive and unhappy. Realizing I could make the switch and go against more traditional means of 'work' was one of the best decisions I've ever made.

Dan Shure
Evolving SEO

Expert Quote - Hire a Bookkeeper

When I started my business, I knew I’d need a crawl, walk, run mindset and practice patience. I didn't know what I didn't know. But in retrospect, I wish I’d hired a bookkeeper right from the start so I could learn from my numbers as I grew and from when I hit potholes. After hiring my bookkeeper extraordinaire, my business grew and it freed me up to do the work I love with the clients I serve.

Kate Paine
Standing Out Online

Expert Quote - Treat Your Customers Right

Clients often judge you not on your technical skill, but on how you treat them, so treat them like royalty. When they contact you, respond quickly. Adapt yourself to their needs, timelines and work styles. Do more than you promised, better than they expected. Compliment more; complain less. Be gracious and grateful. When something goes wrong, apologize and make it right. Treat them so well, they’d never consider going anywhere else.

Andy Saks
Spark Presentations

Expert Quote - Know Your Own Value

I wish I had known and realized the actual value of my expertise early on so I wouldn't have sold myself short for so long. As often attributed to Eleanor Roosevelt: “No one can make you feel inferior without your consent.” I couldn't agree more.

Paul Klein
Bizable TV

Expert Quote - Hire and Delegate

I would have hired help sooner, before I thought I was ready. The sooner you can delegate all of the things that are outside of your expertise, the things that don't directly produce revenue for your business, the sooner you can focus on the things you love to do...the stuff you went into business for in the first place.

Jen Lehner

Tarzan Kay

I‘m Tarzan Kay, I‘m a copywriting and email marketing expert. And something I wish I had known, I wish I had started doing from my very first day in business, is tracking all of my revenue and all of my expenses in a proper bookkeeping system. And preferably having someone do that for me.

So for my first year in business, I put all of my expenses and all of my revenue into a Google spreadsheet. And by the end of the year, it was really, really messy. And then I hired someone to get me set up in QuickBooks online, thinking I would manage it myself. No, I wouldn’t. I just kept getting busier.

If I could rewind and start the clock over, I would get a proper bookkeeping software from day one, and I would hire someone to do it for me as soon as I could afford it. And in fact, it was one of the first big hires I made in my business and one of the best decisions, something I’ve never, ever regretted. So if you don’t have a bookkeeper, go get a bookkeeper. You’re going to need one.

Rich Brooks
flyte new media

If there is one piece of advice and one piece only that I could give to my younger self, something I know now that I wish I knew then, it’s this… get help. No, seriously. As soon as you’re able, or maybe even before, you should be hiring people or hiring contractors or consultants to take over things that either you’re not good at or you don’t enjoy.

I thought originally that I had to learn everything, know everything, and do everything, to be able to succeed. And that is actually the opposite of the truth. As soon as I started using outside consultants, financial consultants, bookkeepers, as soon as I elevated my project manager to be my Director of Operations and more or less run the day-to-day of the company, that’s when all of a sudden we started to grow, and I started enjoying what I‘m doing so much more.

So again, as soon as you’re able, start hiring people. Whether they’re internal people, or contractors, or consultants, or vendors, whatever it is, get that stuff off of your plate and onto somebody else’s who’s better at it and enjoys it more than you do.

And if I give one more piece of advice to my younger self, always get a haircut before recording an important video.

The Advice I’d Give My Younger Self

Hopefully you found some good advice that you can put to use in your own business, regardless of what stage you find yourself at. 

As I mentioned earlier, there are so many things I know now that I wish I knew then…and I’m learning more every day! But if I could only choose one…..

Get Help Where You Need It

This certainly isn’t original, but hire people for everything you can afford. No one is an expert in everything. For me, financials are a bear. Luckily I had an accountant already, and I hired a bookkeeper early on. However, I wish I had hired seasoned financial consultants earlier on to help me navigate that part of my business…a part where I was weak.

I’m also not great at creating (or sticking to) systems. Thankfully, I now have a Director of Operations who handles most all of our banking, HR, medical plans, and basically runs the day-to-day operations of the business, allowing me to focus on what I do best. 

Expert Quote - Rich Brooks

Rich Brooks is founder and president of flyte new media, a digital agency in Portland, Maine, that’s been in business for 25 years. He is a nationally recognized speaker on entrepreneurship, digital marketing, and social media.

He founded The Agents of Change, an annual conference and weekly podcast that focuses on search, social & mobile marketing. He recently co-founded Fast Forward Maine, a podcast and workshop series for growing Maine businesses.

Rich is the author of The Lead Machine: The Small Business Guide to Digital Marketing, a popular and well-received book that helps entrepreneurs and marketers reach more of their ideal customers online.