AdviceCEO Nugget

30 Entrepreneurs Share What They Would Tell Their Younger Business Selves

If you had the opportunity to hop into a time machine and talk to your younger business self, what would you say? Many successful entrepreneurs have shared that they wish they had known certain things earlier in their careers. It could be advice about time management, prioritizing their goals, the importance of networking, or the need to focus on self-improvement. Whatever the advice may be, it's clear that every entrepreneur has experienced lessons they wish they had known sooner. By reflecting on past experiences, you can gain valuable insights to apply to your current or future business endeavors. This is one of our favorite questions here at CBNation.

Here’s what CEOs would tell their younger business selves.

#1- Adopt cutting-edge methods

Photo Credit: Jamie Irwin

If I could give my younger self some advice, it would be to adopt new technology and always be one step ahead of the curve. Technology has a bigger and bigger role in defining how firms operate and compete in today's dynamic business environment. Keeping abreast of technological developments will put you in a position of strength and allow you to perform at the top of your game. While calculated risk-taking is essential to economic success.

Thanks to Jamie Irwin, TutorCruncher!

#2- Self-acceptance reminder

Photo Credit: Sukhy Dhillon

I would tell my 16-year-old self that despite his anxieties about himself as a male and his personal deficiencies, which he was constantly reminded of growing up in the home he grew up in, he is already a good enough person who doesn't need to be the clown to gain positive attention and tell people what they want to hear in order to get their love. Remind him of the truth that he already deserves love in spite of his flaws, limitations, and weaknesses, and that he will never have to go out of his way to win it from
anyone else ever again.

Thanks to Sukhy Dhillon, E-Careers!

#3- Choose who to receive advice from

Photo Credit: Hannah Roper

Many people will be out there, from other business founders to family/friends and strangers on social media, happy to hand out advice and feedback on you and your business. Be selective, no one else is on your journey! Of course, there will be commonalities across businesses and great information out there which will help you grow but when listening to advice ask yourself this, ‘does it aligns with my business model and ethos?’ and ‘is this person’s intention one of development, compassion, and support?’ if so then listen, if not then politely thank them and walk away!

Thanks to Hannah Roper, The Female Creative!

#4- Establish solid ties

Photo Credit: Sanjay Gupta

There are many things I wish I could tell young Tim, but if I could only impart one piece of advice, it would be this: Make friends wherever you go, whether it's at school, work, or play. To a large extent, your network determines the success of your firm, and a contact you made years ago could turn out to be invaluable to your startup. Hence, choose your friends wisely and only hang out with those that won't bring negative energy into your life.

Thanks to Sanjay Gupta, Santa Medical!

#5- Embrace imperfection

Photo Credit: Jeanne Omlor

I would have worried less about everything being perfect. Massive, messy action has gotten me so far in the last few years. Just taking enormous amounts of action and embracing the “Fail Forward” philosophy that it’s more than good to fail- it’s a tool for growth. Taking what you learn from failing makes processes better and better and using this data with each iteration is what leads to success piling up. Not to mention that the
the practice of focusing on growth over perfection develops you as a business person and human being.

Thanks to Jeanne Omlor, Jeanne Omlor International LLC!

#6- Not to be afraid of failure

Photo Credit: Sam Underwood

One piece of advice I would give to my younger self as an entrepreneur is to not be afraid of failure. Failure is a natural part of the entrepreneurial journey, and it is through our failures that we learn and grow the most. Instead of fearing failure, embrace it as an opportunity to learn and pivot your business strategy. Remember that success is not about avoiding failure, but about how you bounce back from it. So don't let the
fear of failure hold you back from taking risks and pursuing your goals. Have faith in your abilities and keep pushing forward, even when things get tough.

Thanks to Sam Underwood, Bingo Card Creator!

#7- Stop having an employee mindset

Photo Credit: Kellie Emmett

Stop thinking like an employee and trading time for money. It's important that you make the shift from an employee mindset to an entrepreneur mindset. I struggled to think that my years of experience were still around an hourly rate and if I charged a certain amount that I should be putting in all these hours to compensate, not what my knowledge and skill set was worth. I took years to get good at what I do, so now I can reward myself with the luxury of something that may take others hours to complete, that I may only take a fraction of that time and it feels good.

Thanks to Kellie Emmett, Trek Digital!

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#8- Focus on building a strong team

Photo Credit: Brandon Mackie

As an entrepreneur, my CEO nugget to my younger business self would be to focus on building a strong team from the start. It's easy to get caught up in the excitement of launching a business and overlook the importance of assembling a group of talented and dedicated individuals who share your vision and values. In my current venture, I've found a superstar team that I gel with very well and we've been able to accomplish some incredible things. We share a love for the sports industry we work in and are all committed to our company's mission, which is essential for long-term success.

Thanks to Brandon Mackie, Pickleheads!

#9- Stay focused

Photo Credit: Henry Purchase

If I could hop into a time machine and tell my younger self something, it would be to always stay focused on the why. Too often, we get wrapped up in the what and lose sight of the why. The why behind our businesses is why we started them in the first place. It's what drives us and keeps us going. It's what makes us passionate about what we do. And it's what's going to help us succeed in the long run. So, be sure to stay focused on the why. It'll help you stay motivated and on track, and it'll help you achieve your goals.

Thanks to Henry Purchase, Menuzen!

#10- Prioritize people

Photo Credit: Kevin Rowe

The mistakes I’ve made as an entrepreneur have cost millions, that I can’t get back. But hopefully, my experiences can help others avoid the same. I’ve spent, or wasted, over $1M integrating technology into my processes to make them more efficient and salable. These include buying existing tech or building my own custom solutions. If I went back in time to 2018 I would tell myself to invest in hiring and retaining great people instead.

Thanks to Kevin Rowe, PureLinq!

#11- Don’t be afraid to pivot

Photo Credit: Kim Walls

If I could go back in time, I would give myself the confidence to change my career path as I saw fit. After graduating from college I was working for a wellness tech startup, but I eventually pivoted to starting skincare companies of my own. I would like to tell myself that it will all work out. If I hadn’t pivoted then I wouldn’t be where I am today. It was a great decision and I’m glad I took a chance.

Thanks to Kim Walls, Furtuna Skin!

#12- Put things into perspective

Photo Credit: Josh Bunce

I’d say, things seem worse at the time and nothing is really that bad. No matter how bad your worst day is, you’ll get through it, and you won’t think about it in five years’ time even if it feels massive today. Time has a way of putting things into perspective, and what seems like a major setback or problem today will become a distant memory. It's important to keep this in mind when facing difficult situations and trust that you have the strength and resilience to overcome them.

Thanks to Josh Bunce, iuf Group!

#13- Prioritize community building

Photo Credit: Radhika Gupta

When I was starting out, I was so focused on driving sales and conversions that I neglected the importance of cultivating a loyal following of brand advocates. I wish I could go back and tell myself that the real value of content marketing lies not just in driving transactions but in building meaningful relationships with customers. I would remind myself that the best way to create lasting impact is to create content that is valuable and engaging and to foster a sense of belonging and community among our audience. By prioritizing community-building, we can create a tribe of loyal followers.

Thanks to Radhika Gupta, One Digital Land!

#14- Upskill as frequently as you can

Photo Credit: Andrew Tomson

I would tell my younger self to attend as many development programs as possible since, in business, there's always something to learn or improve. When I founded my company, I had a fair amount of business experience. Hence, I believed I had all the needed skills and did not need to attend learning events. When I finally went to my first one on a friend's invitation, I realized I had been missing out on a lot. Since then, I have learned things that would have been a game changer had I learned them in my younger business years.

Thanks to Andrew Tomson, Sofilmar!

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#15- Trust your gut

Photo Credit: Mark Wenger

I would advise my younger self to trust your gut. If you have strong instincts, it will help you make better and more informed decisions. I have realized after so many years that trusting your gut limits self-doubt. You don't need to trust so many voices that echo in your head while making decisions. I have been a victim of that. It pushes people toward negative thoughts and ultimately leads to failure. As an entrepreneur, I would say that you should trust and believe your gut instincts; they will never disappoint you. Consider the situation, then listen to your gut.

Thanks to Mark Wenger,!

#16- Let curiosity be your compass

Photo Credit: Rob Barratt

In business, it's easy to get stuck in your comfort zone or fall back on the lazy advice of ‘follow your passion and the money will follow'. But, oftentimes, when passion becomes your north star you can become so focused on your one area of interest that you miss out on other opportunities. However, when you follow your curiosity, you open yourself up to new experiences and unexpected knowledge. You'll find yourself exploring uncharted territories and uncovering hidden diamonds that you never knew existed.

Thanks to Rob Barratt, The Industry Leaders!

#17- Never underestimate the value of networking

Photo Credit: Matt Bigach

If I could hop into a time machine, I would tell my younger self the importance of networking. Initially, when I began my venture, I was a lone wolf and believed that I could take on the challenges without needing help from anyone. I couldn’t have been more wrong. I underestimated the value of having a strong network, but later I realized that having a good network opens up a world of opportunities. I wish I could hop into a time machine and tell myself that seeking help from others isn’t a bad thing.

Thanks to Matt Bigach, We Buy Houses For Cash!

#18- Embrace failure

Photo Credit: William McGrath

If I could give advice to my younger self as an entrepreneur, I would tell myself to embrace failure as an essential part of the journey. It's easy to associate failure with weakness, especially in a culture that values success above all else, but the truth is that failure is a necessary step on the path to success. Rather than seeing failure as a reflection of your abilities or character, see it as an opportunity to learn, grow, and improve. Embracing failure cultivates resilience, perseverance, and a growth mindset that will help you navigate the ups and downs of entrepreneurship.

Thanks to William McGrath, Classy Women Co!

#19- Stay curious

Photo Credit: Andrew Johnson

If I could meet my younger self, I would tell them to stay curious. As a young child, I was always very curious. I would spend hours reading books about the world and its mysteries. My curiosity led me to learn a lot of new things every day. But video games led me astray. My gaming addiction wasted a lot of my time. I would tell myself to reignite my curiosity. Read more books. Go out and meet different people. Go to the library. Just stop playing video games all the time.

Thanks to Andrew Johnson, Prime Seamless Gutters & Roofing!

#20- Test the waters

Photo Credit: Troy Shaffer

As a young entrepreneur, I used to take financial risks without a second thought. This taught me how to improvise early on in my journey. However, this was accompanied by a great deal of financial loss. I would tell my younger business self to do a cost-benefit analysis before making decisions related to marketing campaigns and business partnerships. By doing so, I would’ve been able to direct my time and money toward more meaningful pursuits. I had to learn this the hard way, through a lot of experience.

Thanks to Troy Shaffer, Blu Corporate Housing!

#21- Avoid self-doubt

Photo Credit: Christine Peck

Don't waste another moment on imposter syndrome. It is about as useful as a stick in the eye. Get your strong, smart, curious, problem-solving self out into any industry that intrigues you, and go from there. I waited until I had my MBA and other experiences that had outward validation until I was courageous enough to go into entrepreneurship. While those things can be useful, ultimately, it is perseverance and tenacity that make winning possible. You've got this!

Thanks to Christine Peck, St Hildie's!

#22- Take control of your schedule

Photo Credit: Ryan Rottman

As an entrepreneur, it is easy to try to delegate various tasks as the many responsibilities can seem overwhelming, but if I were to give one piece of advice to my younger self it would be to never relinquish control of your schedule. When I first started, much like today, I constantly had demands on my time, but sometimes made the mistake of delegating my scheduling to an assistant or another team member. This led to interruptions in which I often found myself having difficulty getting what I needed to and never having a free moment.

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Thanks to Ryan Rottman, OSDB Sports!

#23- Dream bigger, take chances

Photo Credit: Dawna Jarvis

If I could go back in time and talk to my younger business self, I would advise myself to dream bigger and take more chances. I would encourage myself to seek out mentors and advisors who have achieved success in their own right and to avoid taking advice from those who aren't where I want to be in life. The business world is constantly changing, and it's important to stay adaptable, open to new ideas and opportunities, and to keep pushing forward, no matter what challenges may arise.

Thanks to Dawna Jarvis

#24- Be patient & learn

Photo Credit: Ben Michael

If I had a time machine, the one thing I would try to get my younger self to internalize is that success takes time. Frankly, I wasn't ready to start a business when I first developed a desire to launch my own business. I spent the first several years of my career absolutely demoralized to be working for someone besides myself, and resenting every minute of it. I was also learning a lot that would help me when I actually did get my business off the ground.

Thanks to Ben Michael, Michael & Associates!

#25- Build relationships

Photo Credit: Jonathan H. Westover

If I could offer a piece of advice to my younger business self, it would be to prioritize building strong relationships with clients and colleagues. Networking is important, but it's not just about collecting business cards or making small talk at events. It's about genuinely connecting with people, understanding their needs, and finding ways to help them succeed. Building relationships takes time and effort, but it's worth it. It can lead to repeat business, referrals, and partnerships that can help your business grow.

Thanks to Jonathan H. Westover, Human Capital Innovations!

#26- It's okay to be the boss

Photo Credit: James Green

Your employees will actually respect you more when you act like the boss instead of another employee. Much like children need boundaries, adults need boundaries as well. When you act like the boss and clearly outline the boundaries your team is to operate within, you're going to have less drama and more productivity. This was a lesson that admittedly took me too many years to learn. For my younger self, I would say start acting like the boss right away. Your employees will follow a strong leader.

Thanks to James Green, Build A Head!

#27- Build a D2C brand first!

Photo Credit: Marc Werner

Looking back as a now 65-year-old CEO, I would advise my younger self to prioritize building a D2C (Direct-to-Consumer) brand before pursuing the wholesale white-label route. While the latter provided quick revenue, it limited our ability to build a strong brand from my inventions and establish a direct relationship with customers. In today's market, DTC is key to success, so start with it!

Thanks to Marc Werner, GhostBed!

#28- Gratitude and risk-taking

Photo Credit: Rick Hovde

If I could hop into a time machine, the first thing I would tell my younger business self is to be grateful for every little bit of success. It doesn't matter if you're starting out small – your work ethic and dedication will ultimately bear fruit. I would tell myself to stay focused on the goals that will bring you long-term happiness, rather than achieving short-term success at all costs. I would also say don't be afraid to take risks – sometimes risks pay off in incredible ways if you trust your instincts and go for it!

Thanks to Rick Hovde, Hovde Dassow + Deets!

#29- Seize opportunities

Photo Credit: Aaron Jerez

If I could go back in time and talk to my younger business self, one of the most important things I would tell my younger business self is to never waste a moment. Every day is an opportunity to learn something new, make something better, and continue to grow your business. No matter how challenging it seems, never give up and always believe in yourself. This might be a simple statement to some, but when I started my business, I had a lot of doubts and hesitations.

Thanks to Aaron Jerez, Home Bar Select!

#30- Self-reflection

Photo Credit: Marc Morego

Jumping into a time machine, I would first tell my former business self to take the time to identify my weaknesses and strengths. Invest in what I am good at. Honing in on those skills will pay off more than shoring up my weaker abilities. Identifying your strengths and staying true to them is essential to maintain a sense of direction during times of uncertainty. Having an honest understanding of who you are and your unique perspective will give you the best chance at making your dreams come true.

Thanks to Marc Morego, Service Club Delivery!

If you could hop into a time machine, what would you tell your younger business self? Tell us in the comments below. Don’t forget to join our #IamCEO Community.

Ashok - CBNation Team

This is a post from a CBNation team member. CBNation is a Business to Business (B2B) Brand. We are focused on increasing the success rate. We create content and information focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts, ( and videos ( CBNation is proudly powered by Blue16 Media.

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