When you start your own business, it’s a liberating feeling. Now, the burden to bring in clients and grow the business is on your shoulders. But know this, you’ve got this, and you’ve got help. In her new book, Just Go With It, entrepreneur, CEO and innovator, Mandy Gilbert shares her journey to guide and inspire both new and established entrepreneurs alike.
She shares hard-earned lessons on how to strike that perfect balance between managing your personal life, developing your people, and maintaining a healthy bottom line, all while making time to care for yourself. To Mandy, entrepreneurship is definitely an adventure worth taking, even if the path is rarely a straight line.
Drew Appelbaum: Hey listeners, my name is Drew Appelbaum and I’m excited to be here today with Mandy Gilbert, author of Just Go With It: How to Navigate the Ups and Downs of Entrepreneurship. Mandy, thank you for joining, welcome to the Author Hour Podcast.
Mandy Gilbert: Thanks Drew, happy to be here.
Drew Appelbaum: Let’s kick this off. Can you give us a rundown of your professional background?
Mandy Gilbert: Sure. I dove into entrepreneurship at a pretty young age. 2002 is when I started my company, which is a recruitment firm purely focused on advertising, marketing tech, digital, and design. So, I’ve been doing that since 2002, and prior to that, I was in a number of, junior to intermediate level marketing roles within different organizations.
Drew Appelbaum: Now, why was now the time to write this book? Did you have some free time because of COVID? Was there an “aha moment” or an inspiration out there for you?
Mandy Gilbert: That’s a great question. So, this book has been in progress for over a year now, and my motivation for writing it really was to share my experiences. I think that being an entrepreneur can be incredibly isolating, you can feel incredibly vulnerable, and the highs and lows are quite extreme. So, through my speaking career, I’ve connected with so many entrepreneurs who thank me for being so honest about, not only how I’ve had to overcome challenges, but really sharing the depth of the challenges themselves.
There’s that relatability component that I think the audience and fellow entrepreneurs benefit from.
Drew Appelbaum: Now, did you have any major learnings or breakthroughs that were unexpected while you were writing the book? Maybe through doing some research or just by looking back at your journey?
Mandy Gilbert: I did have some–I don’t know how many breakthroughs I had but I certainly had some micro-breakdowns. Definitely going through the past and reliving and really opening up memories of challenges and mistakes that have been part of my journey. And, really digging deep and sharing that and talking about how I was able to overcome them or not.
It was a really interesting journey to go through that timeline and revisit the main events as well as my own growth and development throughout my entrepreneurial life thus far.
Drew Appelbaum: Now, who is this book for? Is it only for entrepreneurs and executives?
Mandy Gilbert: This book, I think definitely talks to entrepreneurs or individuals thinking about being entrepreneurs, whether it’s a side hustle or if you want it to be your main focus. But it also can really connect with people really taking on management leadership positions.
It is woven through the book, definitely my development and some of the mistakes that I’ve made as a young leader and how I’ve had to grow in that area to have a sustainable team, to have a sustainable business, and one that’s solid enough that you could build on.
Drew Appelbaum: Now, a lot of people write a book, almost for their former selves, usually because there was some adversity along the way. Can you tell us about a few of the issues you ran into earlier in your career and maybe some of the lessons that were learned?
Mandy Gilbert: Sure, I think a lot of people like myself, take the plunge of entrepreneurship. Maybe it’s for reasons that include you have something to prove in life–whether it be to yourself or to others. It could be, you’re incredibly passionate about what you are doing or your idea and you want to innovate it and do something and drive that and have control over the outcomes as much as you possibly can.
So, for me, my motivation for writing the book and some of the challenges I’ve had to overcome earlier on, when I was a great salesperson, and I was a great recruiter. And that’s great when you first start your business because you get some traction and you’re great at what you do.
The complexity and the challenges that are layering on, when you have to think about, “Oh goodness, finances. How do I scale at technology?” And all of those things you navigate through hiring various expertise or consultants. But the tricky one was, “Well, how do I lead a team? How do I curate some type of vision and goal for the company that connects everyone who is part of it? And how do I really foster a culture that is going to be something that sticks and grows and builds?”
Some of the things that I stumbled on were how to show up as a leader. I wasn’t sharing a lot of my worries, I wasn’t sharing a lot of my concerns and things that were just keeping me up at night, as well as my own insecurities. I was carrying it all on my back and I was also having a very difficult time at that point in my life having and embracing difficult conversations and giving direct feedback.
How that started showing up is that I was becoming a little bit passive-aggressive, I would say one thing and do something else. I also have a quick start, I’m an idea person, I get a lot of energy from ideas and so, I was also starting a lot of initiatives and then dropping the ball and not completing them.
Or worse than that, I was delegating my ideas and then not following through and I was wasting people’s time. I think over time, that really hurt my leadership brand internally, certainly. As a result of that, I had some pretty significant culture challenges as well as some turnover in the earlier years.
Building Your Own Success
Drew Appelbaum: You also talked about that you are given a leadership position earlier in your career but found yourself as you’ve just mentioned, afraid to speak up, not getting the respect you deserved, and even a victim of harassment. So, you decided to open up your own shop. Can you talk to us about the decision to leave that job you had and what the transition to business owner looked like for you?
Mandy Gilbert: For me, the motivation was that I knew at a young age that at that time, it was probably the right time for me to take the plunge, and I had thought about it for a long time. I was someone who always just worked incredibly hard and posted great results and numbers.
Because of that, I would have the opportunity to join committees and be put up for promotions, which was great. The downside of that was when you get hurt by working for certain leadership styles or somebody’s inappropriate with you, or you see things that are happening within an organization that are not aligned with your own values, it really woke up my desire to go and do something on my own because I was tired of building success for organizations that I didn’t really believe in and that I didn’t feel aligned with.
That’s what really inspired me to open up my business, and really, what that involved was getting a personal line of credit for $8,000. That funded my startup. I had enough to keep me afloat for six weeks. So, my journey started with a computer, I had a hundred and fifty square foot office, slash closet if you will, and a phone. I had 200 pieces of letterhead and a Splash page on my website.
I was really energized by the accountability and the pressure and the risk that I was taking because I believed I could do it. I wanted to have the opportunity to try something on my own, build something that is lasting, that fosters and attracts great talent, and has a culture that is all about growth and collaboration, and creativity in entrepreneurship.
It really was inspired by working with companies that didn’t really have those characteristics or have that kind of energy. It was something I really wanted to do, and I wanted to focus on quality over quantity, and relationships. I also wanted to have a recruitment company that’s not competitive.
Where you are not pitted against your colleagues, instead, you collaborate, and you win a lot more together and you can accomplish a lot more. So, that’s what really inspired me and you know, in the earlier years, that’s really what it was all about–me, at a desk with my computer doing cold calls all day and interviewing candidates to build up my database and my network in the evenings until 9:00, at least every night.
So, it was a lot of hard work, and certainly a lot of hustle. But, at the same time, it was incredibly energizing and rewarding.
Making an Impact
Drew Appelbaum: It’s such an inspirational story. Like you just mentioned, you started with $8,000 and working by yourself out of a closet of sorts. Fast forward to now, how many companies are you in, how many employees do you have, what does it look like?
Mandy Gilbert: I’m still the founder and CEO of Creative Niche, which is the recruitment company that I started in 2002. That business does north of 10 million, we’re a team of 20, and in our time in business, we’ve done over two million dollars of impact work, and we have been behind more than 14,000 successful placements with all kinds of companies and sectors, ranging from advertising, tech, design, products, e-commerce, and digital.
That company continues to do great things, I have a fabulous team, and all of the team contribute to an incredibly positive and productive, and collaborative culture. That, being so solid, has allowed me to also invest.
So, five years ago, I co-founded a digital school. It’s a tech design digital school, which was high growth, I really didn’t play too much of an active role in it but I did contribute a lot and it was all hands on deck, it was also very boot-strapped and it managed to do incredibly well and thousands of students graduated from it.
That went on to do amazing things in UX Digital Marketing, web development, and design. Sadly, that school really struggled with COVID-19 and the implications for bricks and mortar education and sadly, it didn’t survive. That operation closed in April. That was incredibly tricky for a number of reasons, obviously, as an investor.
Financially, it’s a big hit. But equal or more than that, it was really sad to see it because it was a pretty incredible place, it was a very special place where the outcomes in student’s lives were so profound, and we had the ability to attract and work with so many amazing instructors. We worked a lot with the community and as part of the curriculum for students, they worked on not-for-profit organizations, branding, and websites.
It did a ton of great impact. Millions of dollars of work done pro bono or for impact organizations and not-for-profits. It was amazing. I wrap it up with a bow that it made a tremendous amount of impact in a lot of different lives and there was a ton of learning in my experience.
I talk a little bit about that in the book, because it was my first time having a business partner and having investors. There were a lot of outcomes from that that I would do differently next venture, for sure. Also, as an investor, I’m a proud investor in two great Canadian tech companies that are doing wonderful things.
I support the CEO’s of those companies, I’m all in, I believe in them one hundred percent, and it’s really great to be an investor and an adviser versus having to actually drop in and do the work yourself. It’s a way of supporting entrepreneurship and working in different sectors without having to be accountable for all of the outcomes as well.
So, I am an active investor and I do some speaking as well, and I’m also a columnist with a .com. We have a weekly column where I talk about entrepreneurship, leadership, management, culture, and all of those important things, which I really enjoy as well.
Drew Appelbaum: Well, I’m sorry to hear about the RED Academy but it sounds like you’re still doing very, very well. They did a lot of good in the community and that’s really great to hear. I would love to bring this back to Creative Niche and the book. And, in the book, you talk about your original employee handbook, and I was wondering about that original employee handbook, and how it has evolved over the years?
Mandy Gilbert: Sure. You never think that something would be so helpful when you’re starting and building a company. I think it started because of a funny story of an employee I hired, a young employee who didn’t do a couple of obvious things–that if you had any experience, you would have thought of them when you showed up to work.
I won’t detail them but that tends to be when we put in policies–when somebody makes a mistake or does something ridiculous. That’s when I really built that out, it was really in my early days. I just wanted clarity. I mentioned earlier, having difficult conversations was not a strength of mine that I really was comfortable with in my earlier years. And so, I liked having clarity and having something to point to.
When you have something to point to, “Hey, I’m not being the bad cop, and you know what’s expected of you.” I built it out because it was needed and I thought it would be a really professional way to onboard new employees too, to talk about the values of the company, how you are differentiated, and how you are expected to show up. Also, how I am expected to show up and how we treat our equipment, and how we spend our time.
Also, what does success look like for the company and what does success look like for your role? I thought, in my experience, if I were starting a company, that would be a really impressive way to understand exactly what the company is all about.
Then, as an employer, it’s a great thing to have in place, and you can say, “You know what? Actually, we did talk about this, and it is in the handbook, so why don’t you have another read?” It kind of helps mitigate things that normally you might have to address on a regular basis.
And it’s evolved. Policies change, procedures change, rules change. So, it is something that we take off the shelf, the digital shelf if you will, once a year. As a leadership team, we look at it and we talk a little bit about, “Is there anything in here that we need to update or remove?” We do it on an annual basis and that way, it’s a living document and we all refer to.
Opportunities to Revisit
Drew Appelbaum: What are some of the tough questions that entrepreneurs should ask themselves to make sure they’re providing a great experience for their employees?
Mandy Gilbert: You know what? That’s such a great question that sometimes I do ask entrepreneurs. Because oftentimes, we think we’re amazing, we think our companies are incredible, and that we’re the best, and nobody else is going to care as much as we do for our employees and for our clients.
We lose sight of what other companies are offering, and are we really that amazing? Do the perks that we offer really matter to our employees? How much bias is there? I always recommend that you unpack your employment or your employment experience, for everything from your job posting when you’re recruiting to your offer letter, to how you onboard new staff. Now especially, how are you onboarding virtually to keep them engaged and a part of the culture?
So, once you look at every step, there’s always opportunities to revisit. There’s a lot of creative ways that entrepreneurs can change their offering because we have the flexibility, and we can be agile, and we can be creative. So really, just spending some focused time and thinking about, “How can I be an incredible employer?” And, “How can I have the best employer brands?” So, when my employees and my team are out with their friends and out with their colleagues in the industry, they’re talking about the company.
I want them to say great things about how they’ve been able to grow, how they’re supported, how they’re acknowledged, and some of the other benefits and perks. All things that are part of that whole experience. I think it’s an interesting project.
Drew Appelbaum: One of the hardest things to do is look into the mirror and really see what you as an entrepreneur are bringing to your own company and what your role should be. So how could entrepreneurs find out the value and their unique role they’re supposed to be providing to their companies?
Mandy Gilbert: Yeah, that’s a big one. Because I think our roles really change. In the earlier years, when you start your business, you might have to be incredibly exceptional. You might be part of delivery, you’re rolling up your sleeves, you’re doing the work, you’re hiring, you’re managing, you’re having to wear multiple hats and figure out a number of different things as you go along.
I think that’s just the norm. Unless you’re really funded when you start, so you can have a dream team out of the gate, which would be awesome, but that’s certainly not what I had. So, in the earlier years, you’re definitely hands-on, you’re part of the team.
I think that some entrepreneurs have a really difficult time popping up and staying up, and what I mean by popping up is not to be the leader in charge and the boss and have that kind of presence in your culture. It’s about thinking strategically, “Where is your business today, how much market share do you have? What are some things big and small you can innovate? Are you leveraging any grants out there? How was your team? How engaged are they? What can you provide as additional service or products to your customers?”
The danger, if you can’t pop up and stay up and work on that high-level thinking at least 75% of your time and you’re popping down, you not only are micromanaging your staff, you’re probably not doing as great of a job at those executional tasks as maybe you think you are.
You’re not allowing space for your employees to feel trusted and actually make mistakes and grow. There’s also that risk, from a culture standpoint, and from a morale standpoint, and growth with your employees if you’re popping down and doing their jobs, or are correcting them or micromanaging them and not really spending your time focusing on your future business, it can result in some risks for sure, and you can kind of get stuck there for a long time.
I think your job as an entrepreneur, always changes, depending on what the business needs. I’ve gone through the great recession. And I have gone through, all of us have, the implications of COVID-19. So sometimes, the business actually needs you to pop down and get with the team and reconnect them and put a game plan in place and help them execute it and build confidence and reassurance with them.
Making sure that you’re communicating and you’re acknowledging and all of those things. But when business resumes, it’s really important that you go back and think about the future and your future business.
Drew Appelbaum: Now, starting a family as an entrepreneur is incredibly difficult–what was your experience like? And how did you navigate the balance of being a parent-preneur as you call it?
Mandy Gilbert: Yes. You know, I sometimes say there’s never the right time to, take a vacation, buy a home, start a business, or start a family. There is never really the right time, you just kind of have to do it and figure it out.
For me, that’s exactly what I did. My business was pretty young when I had my first son, Isaac. I underestimated the demands of a little one for sure. So, Isaac was days old and I had him in the office, and I was doing reporting, and I was working with the team, and having meetings. They sleep a lot at the beginning and then they get active.
I thought, “You know what? I want a maternity leave.” My brain and my heart can’t be in two things and I fell instantly in love with both my sons. I really wanted to have a leave and so, I hired up to support me so I could take a maternity leave, which was amazing.
I thought I had my hands full with one little guy, and two and a half years later, I had my second guy, Samuel. That was tricky, and parenting and running a business is really difficult. Because when the times are really good and you’re scaling, you feel really engaged, and you’re busy it’s really difficult to shut that brain off when you come home and be present.
For me, I had an office in Europe, I was traveling a lot, and then my speaking career, I was also traveling. The guilt associated with that and the fear of missing a fever or missing a performance at school or a tough day, it’s always top of mind.
But I think the most important thing is just to be okay to be part of something in your career and feeling really connected and have your individuality and your passion. It’s okay, you’ve got to roll with the punches–life isn’t a checklist.
There are going to be times where you’ve got to drop down and do a lot of work and then those times when things are going great and your team is there to support you and you’ve got a solid business, those are opportunities when you can take a lot of time off.
You can do drop-offs and pick-ups and play dates and maybe little trips with kids to celebrate milestones, or just impromptu trips, or road trips. I think you have to go and figure it out and understand, “Hey, life is not perfect, not everything’s going to be perfect.” But, as long as you are trying your best, trying to cover the basics, that’s all you can do. So, it is definitely a tricky one to navigate but it’s definitely worth it for those that are thinking about it.
Drew Appelbaum: Now, let me ask you one last question, it’s based on your interactions with many entrepreneurs, it’s a pretty easy one but tricky as well. Do they all know what they are doing? And, should an entrepreneur feel bad if they’re struggling right now?
Mandy Gilbert: You know, sometimes you don’t know what you’re doing, that’s why sometimes we’re unemployable after you’re an entrepreneur for so long. Because you’re just like, “I’m going to do marketing. Hey, what’s going on in marketing? I think we need a new tech platform. Oh, I got it. How’re sales going?”
You’re constantly getting your hands in everything and sometimes you go through phases where you’re just incredibly unproductive. Because you don’t have a job description, you don’t have a boss, and quite frankly, you don’t have any peer accountability. You’re not getting calls from performance reviews, right? And you can get out of anything that you want to get out of. I mean, really, there’s not a ton of accountability other than paying bills and keeping the business going.
It can be tricky and I’d be lying if I said that I’ve never fallen into a slump. I have, and I have left work feeling like, “Wow, I didn’t accomplish a lot this week, oh another week, but I’m here and I should be out with my kids and I haven’t seen my friends in a long time, I’m not really hitting any home runs in my life, I feel bad about not being with my family all the time but when I’m at work, I’m not that effective and I’ve left some friendships and relationships be ignored.”
So, it’s important to have a reset and understand, what is the most valuable thing that you can do for your company that actually gives you energy? And if you’ve lost sight of that, that’s a great opportunity to ask people who know you best.
You can also ask, sometimes, your leaders in your company, or if you don’t have any leadership team yet, you can ask your employees, “You know, where do you see me, how can I help?” Also, join some organizations, such as an entrepreneur’s organization or as you scale, a YPO, young president’s organization.
They are amazing places that give you inspiration because you’re with peers. That gets you excited, “Wow, I never thought of that, or I need to do that.” It can help us create a little bit of energy and focus into your role if you find it continuously lagging and you’re not feeling focused or impactful.
Drew Appelbaum: That’s some really great advice. And Mandy, writing a book, especially like this one, which will help so many business professionals is no small feat, so congratulations.
Mandy Gilbert: Thank you, thank you so much.
Drew Appelbaum: The last question. If readers could take away only one thing from the book, what would you want it to be?
Mandy Gilbert: It would be, you don’t start a business to work harder than you’ve ever worked and not make money. That’s a lot of motivation, we want to have more control over our lives, we want to have a steady and healthy income, we want to enjoy ourselves. And, I think that the big takeaway is to honor that and invest in yourself. You are worth it.
Invest in yourself to grow and develop, embracing direct feedback on how you can become better. Enjoy the experience because the highs are high, but the lows are low. So, you want to make sure that when things are going well, you’re really enjoying your life and you’re taking care of yourself, you’re taking care of your team, you’re taking care of your family, and you’re enjoying yourself.
That’s really a big reason why I wanted to share my experiences because I’ve seen so many entrepreneurs struggle. I think being rooted in why you decided to do this, and making sure you’re valuing yourself and investing in your development and happiness is incredibly important.
Drew Appelbaum: This has been a pleasure and I’m so excited for people to check out this book. Everyone, the book is called Just Go With It, and you can find it on Amazon. Mandy, besides checking out the book, where can people connect with you?
Mandy Gilbert: They can connect with me on my website, mandy-gilbert.com, and on Twitter, @verynichey is my handle and my email address is [email protected].
Drew Appelbaum: Awesome, Mandy, congratulations again on your book and thank you for coming on the show today.
Mandy Gilbert: Thanks Drew, thanks for having me.