Allison LaGuardia of ALL Media On How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

An Interview With Jake Frankel

Embrace Entrepreneurship- I always have friends saying how amazing I’m doing at my job is and that I took such a risk, but I honestly never felt l couldn’t do it. I always believed in what I was doing, and I knew I could do it. It is scary financially to take the leap, of course, but if you really prove it out that it is a business someone needs and sees as something valuable, you will do great at it.

Being a founder, entrepreneur, or a business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experiences. I had the pleasure of interviewing Allison LaGuardia.

Allison LaGuardia is the founder of ALL Media, a strategic firm providing a launchpad for ambitious founders and emerging brands. Her company crafts custom-tailored integrated campaigns that skyrocket brand awareness by combining holistic media expertise with deep category insights. ALL Media’s goal is to level the playing field, empowering courageous startups to breakthrough as industry leaders through innovative media strategies.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Sure, it wasn’t a conscious decision to become an entrepreneur. To me, the moment I knew was when the agency I was working at was bought by private equity and the new owners told us to say goodbye to the small fish and to start “hunting elephants”. That it was hard to let go and no longer work with about 250 clients. I knew deep down inside that I wanted to continue to help the emerging brands and founders with my expertise in navigating the bigger budgets and standing out which was ultimately my decision to start ALL Media to focus solely on that.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

When I left the agency to go to a digital publisher back in 2013, my job was to bring new boutique brands to the publisher. However, I kept getting asked by the clients I was working with if I could also help them with a billboard or with a guest podcast opportunity which was NOT something I could do for them while at this company. A colleague of mine who was a managing partner at one of the top consumer private equity companies and I had lunch and he said “you can do this. You can set out to help so many brands because no one else is paying attention to them and no one else has your experience”. I sat on the train home and said, “YES I CAN”.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later? Can you explain what you mean?

I never thought of myself as a natural born entrepreneur, but the older I get, the more I think maybe I am! I am always thinking like an entrepreneur, but I would have thought it was more like a salesperson. You realize those are hand in hand with marketing and selling a product and really knowing and listening to what a consumer’s pain points are. Problem/Solution is always at the root of the campaigns we work on.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

There are so many. If I had to name one, it would be John Kenney of Cult Capital who I mentioned already. He was the one who told me I can do it and believed in me and never wavered! He is such a busy man and super smart and, in the beginning, he would always take my calls and he would give me advice and really was more support than he knows!

What do you think makes your company stand out? Can you share a story?

I really believe it is our service. We talk to everyone for hours sometimes. Listening and learning and really getting to know our clients and potential clients. We are also really great connectors. I believe in helping people and one of my clients taps me for employees or jobs and calls it my side hustle because I will always refer people and pay it forward. I believe in it.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Grit- In the beginning, I had no extra money when I first launched. I would book my schedule with tons of meetings for one day in NYC and bang them all out. I would walk to EVERY SINGLE ONE and I would call my Mom and say “I’m walking to my next appointment”. And she said to me “one day you will be able to afford to take a taxi Alli, just keep doing what you do and it will come”. Now I do it sometimes just to remember those days!

Flexible- Every client is different and as much work as it is to build a new proposal and media strategy every time, there is not one company that is alike. There is no template for a new business call. It’s all from scratch and thoughtfully produced with the client in mind and that clients’ goals.

Patience- Early on, I learned that every loss becomes a lesson. Some things take time and working with all different brands and founders at all different stages of their business, that it is sometimes not going to be on my schedule and that is ok. I’ve learned that if I am producing good work and staying true to our core, you realize that sometimes you aren’t going to be a good fit for everyone and in turn, they may not be a good fit for us as well. That is ok.

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

Let them have a chance to do the work without being micromanaged. They need to fail to make mistakes in order to learn. Let them learn.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Spending too much money on unnecessary expenses. Really focus on what will drive the business forward and only that. Do not make purchases until you are profitable and can reinvest in the business.

Ok fantastic. Thank you for those excellent insights. Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

I think when you have a regular job, there is always a fall back. It may be a team, it may be a hierarchy, it could be job security or whatever it is that when you make a mistake, you can take a breath and move forward as business as usual. When you are an entrepreneur, you are the fall back. You are the one who takes the fall but also reaps the rewards of the win.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

Of course, it was when I landed my first client. They actually left my old agency, and they were a client there. For them to put their faith completely in me, the first few months of being out on my own was a euphoric feeling for so many reasons!

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

Lucky for me I have not had too many lows. I know how the business works and I expect clients to leave but I always have a pipeline and I’m always networking. That is key. When I lost my biggest account, yes it hurt, but luckily, I gained 3 new accounts which made up for the revenue loss from one account. Very grateful for that.

Based on your experience can you tell us what you did to bounce back?

That was and always is the holy grail called THE PIPELINE! ☺

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

1. Unwavering belief in your Mission: My passion for small to mid-size brands wasn’t just a business plan- it was my core mission. When colleagues questioned my focus (always wanting to go for the bigger ad budgets), my dedication to the mission was always that. Remember that the unique vision is your North Star.
2. Strong Network of Connections: I’ve always said that my connections are my strongest asset. In this industry, they are lifelines to me. Not only for new clients, but more importantly, for support and opportunities and sometimes just a different way of looking at things. Build and nurture relationships is key.
3. Adaptability- In advertising, trends change overnight. I’ve had to pivot strategies countless times, but never at the cost of my core values. Being media agnostic allows me to adapt quickly to new channels keeping clients out in front without losing any momentum.
4. Focus on the client- Make your clients victories shine. I always tell them when they get big and get acquired or they need a bigger agency, I’ve done my job. Their success is my success.
5. Embrace Entrepreneurship- I always have friends saying how amazing I’m doing at my job is and that I took such a risk, but I honestly never felt l couldn’t do it. I always believed in what I was doing, and I knew I could do it. It is scary financially to take the leap, of course, but if you really prove it out that it is a business someone needs and sees as something valuable, you will do great at it.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

To me, resilience isn’t just about bouncing back- it’s about bouncing forward. In my world of media strategy for emerging brands, we are always in challenging times. Big competitors have deeper pockets, trends shift overnight and now we have economic uncertainties. Resilience is the ability to withstand the pressure and us it as innovation and growth.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

Absolutely. I maintain a positive attitude during difficult situations, but it is not innate optimism- its strategic positivity from years of turning underdogs into icons. When challenges come up (which they always do), I revisit past victories and remember how to get through it. My positivity is fueled by the founders we work with- if they can stay optimistic while disrupting billion-dollar industries, then I must do the same!

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

In advertising, especially in our niche of elevating emerging brands, attitudes are contagious. As a leader, your optimism or pessimism doesn’t just reflect reality- it often creates it. When you genuinely believe that your passion, innovation and smart strategies can outmaneuver giant budgets- and you have a track record to back it up- that conviction spreads. It turns clients into visionaries and teams into trailblazers. And in this business, those transformations don’t just boost morale, they often become case studies!

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

“It’s not the size of the dog in the fight, it’s the size of the fight in the dog” by Mark Twain. This isn’t just motivational wallpaper for me, it’s the heartbeat of my entire professional ethos!

How can our readers further follow you online?

My website is www.allmediaboutique.com.

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!