It’s one of the most common questions when it comes to starting a business: do you go all-in or do you do it on the side while keeping your day job? Or maybe it’s some combination of the two? Both sides of the coin can make strong arguments, so we decided to go straight to the source and talk to some real small business owners about how they’re launching, what works for them, and what the pros and cons of their choices are…

Meet the owners of Stiletto Escape and The Pulse, two up-and-coming small businesses out of San Diego, California.

Jana Wallis and Shivani Ballesteros of Stiletto Escape

Stiletto Escape was born out of Jana Wallis and Shivani Ballesteros’ mutual passion for travel, food, and friends, in addition to a desire to have more autonomy in their work lives. Stiletto Escape provides concierge style travel-planning services for girlfriend getaways, solving the planning hurdle for women who want to travel with their girlfriends, but simply don’t have the time to plan the whole thing out. Think of them as expert travelers that are willing to share their “locals only” knowledge with you like a best friend.

Our other featured business is The Pulse, San Diego’s “only interview style video marketing company” led by Cindy Matalucci. Throughout her successful career in sales Cindy kept her eye on the future of digital media. With an effervescent personality and a sharp understanding of how video content could change the world of marketing Cindy gets the 411 on all the latest and greatest things to do in city San Diego. From the newest bars and restaurants to the chicest boutiques, the coolest workouts and gyms, she guides her viewers through it all. Cindy also hosts and covers events for her streaming network (including the 2014 Sundance and Santa Barbara Film Festivals), and hosts an online show based on local fashion in San Diego.

So, how did Jana, Shivani and Cindy all get there? The short answer is “a lot of hard work,” but it goes deeper than that. We sat down to have a conversation with these three women about how they got started…

Do you run your small business while maintaining another job or is it your sole focus?

Stiletto Escape: We both still maintain our day jobs. Shivani is an in-house attorney for a large energy company and Jana is an account manager for a digital marketing firm.

The Pulse: I worked sales and marketing in the corporate world for 17 years. I started my business 3 years ago as a passion project and it turned into a career. I left my corporate job in October 2013 and I am now full time at The Pulse.

What are the advantages and challenges of launching your business while maintaining a full time job?

Stiletto Escape: We did some research to start and that turned out to be the tipping point for us. When we tested our business idea with a focus group of over 50 women the results showed the women were actually interested in this concept, would buy into it, and needed it! After some more in-depth conversations, many hours of research, and a couple “ok, can we really do this?” conversations, Stiletto Escape was born.

We’ve both kept our day jobs since the launch, so we enjoy the benefits of having a steady income to support ourselves, the ability to generate additional capital to get our business off the ground. But maintaining your day job can also provide growth, skill development, and on-the-job experience that is integral to building your business.

For us, one of those assets when we were starting out was Shivani’s legal background and her ability to properly apply for our LLC and setup our business agreement, as well as create standard client contracts and operating procedures. Another was Jana’s exposure to web development and digital marketing which gave us a strong foundation for our website and following best practices online.

The Pulse: I would have to say launching my business while still working my corporate job really helped finance my company in the beginning. I did not need to go to investors and I had the extra money to buy equipment that I needed to get my business off the ground. I was also able to pay for items like marketing materials, attendance fees for networking events, and dues to groups so I could make the connections I needed to grow my business.

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Cindy Matalucci of The Pulse

What are the advantages of launching your business without having another full time job? What are the challenges?

Stiletto Escape: Without another job, you can devote all of your time and resources to launching your business, acquiring clients, and growing your marketing strategy. However, you also have some sense of “this has to work” urgency, since your success depends solely on you and your idea. There is no reward without risk; not having a safety net forces you to swim, but at the same time, if you have another job, the fear of sinking isn’t as paralyzing.

The Pulse: For the first two years this worked out great, but then I started finding myself burning the candle at both ends, working my corporate gig by day and working at my own company on nights and weekends. You start off so excited, just running on adrenaline because you are so passionate about your business. Eventually you start to get burned out and realize that your day job is hindering you from really living the life you were born to live.

Suddenly I just hit a point where I’d just had enough of the corporate life and really had the drive to be an entrepreneur and work for myself. I’ve never had a problem with self-motivating and really wanted to throw myself into my company full force and see what I could create and where I could take it. The issue is if you never jump in 100 percent and take that risk, you never fully know what you are capable of. I knew if I kept my day job, I would not be able to take my business to the next level. Three years after I started the Pulse, and almost a year ago now, I made the leap into full blown entrepreneur and never looked back.

How did you decide it was time—or decide it’s time—to quit your full time job to pursue your entrepreneurial venture full time? What measures and benchmarks are you using? How did you figure out how much capital you needed?

Stiletto Escape: We’ve each identified a number – the amount for which we’d be willing to walk away from our day jobs. When Stiletto Escape is supporting us to that degree, that’s when we’ll go. Based on what we’re making now, the lifestyle we’d each like to lead, and accounting for where we’d like to be in the future, when that time comes, we each calculated a figure and that’s our main benchmark for knowing when it’s time solely be the owners of Stiletto Escape!

The Pulse: I was making quite a bit of money in my corporate job. I had been at my last company for over 13 years and was very established there. I was a top sales rep and made most of my money on commission. I had socked away for a few months so I had a bit of a cushion. I can’t say I was in a perfect place when I left though.

Looking back, hindsight being 20/20 and all, I should have saved more, but the timing was right for me to branch out on my own. I literally couldn’t stay in the corporate world another second. I looked at my overall living expenses and then compared my expenses against my previous corporate income and also against what I needed to earn in order to survive. I started to cut back on some of the luxuries and items that I didn’t need anymore and looked at ways to minimize my bills.

It’s funny how when you are working for yourself you really prioritize things and what is truly important in life becomes clearer. I found that some things I used to spend money on didn’t seem important anymore, I didn’t even want to spend money on them anymore. I really became focused on how I could put money into my company to improve it. I knew how much income I needed to bring in each month so I broke that down into how much money per week and per day so that I had a daily and weekly goal. If you don’t define and capture your goals, you’ve got nothing to strive for.

What mental hurdles did you need to overcome to strike out on your own?

The Pulse: This was a tough one because I was so used to working for a large corporation that had a big name and great name recognition. I had to build my company’s reputation up one day at a time, so right away that was a mental hurdle for me in the beginning; just not being as confident about my business as I could have been. No one had heard of ” The Pulse” in the beginning so I just faked it until I made it. I went out there and acted like I had been around forever and people took me seriously. It is all in how you carry yourself. Over the next few years I created, filmed, and produced over 250 videos. Then people knew who we were.

I would say another hurdle is not knowing your value. In the beginning I felt like I had to charge less money because people did not know who I was. After a few years of doing business, learning your industry and becoming an expert in what you do, you realize you are worth much more and you start to charge the right amount for your services.

How do you grow your business? How do you find and retain clients?

Stiletto Escape: Our business has largely been built on a strong network of referrals and by word of mouth so far. And since we’re relatively unique in the travel space, people find us on the web when they are searching for niche travel planning needs like bachelorette parties.

The Pulse: Since I had built up such a great network in the corporate world, I really leveraged those connections. My clients from my corporate job became my first clients in my own company. People buy from people they trust and like. You have a great relationship with these people so you talk to them about your business. They become your raving fans, your champions, and your best source of referrals. Networking was always my thing. I started a few networking groups that were extremely active so I just switched from representing my corporate company to representing my company, The Pulse, at the events.

I also came up with strategic vertical markets I wanted to target like restaurants, boutiques, and non-profits. I started joining LinkedIn groups that were in these markets. I even did some cold calling! I also attended events and tradeshows that would include these types of vendors.

How do you get the “office operations”—things like finance, payroll, web/tech support, and HR—done without staff?

Stiletto Escape: Like many small business owners, we wear many hats! We’ve had to learn a lot of things along the way in order to do things like set up client billing systems or learning how to post a blog entry online. But we also rely heavily on independent contractors for things we just can’t do ourselves. For some tasks we’ve been able to trade services, but a large majority of our overhead does go to outsourcing.

The Pulse: For the first two years, it was me and my boyfriend, who I made into my camera operator. We decided to jump in and learn everything we could about the digital video media business. I learned how to operate the camera and edit video myself so I could be a technical ninja and know the ins and outs of my industry. We had a few friends that were photographers that we worked with and contracted for jobs with us. Luckily my boyfriend was a web developer, so I had him create our first website and teach me how to do blog posts and update the site.

All too soon though, I was inundated with every piece of running the business. I was booking clients, attending the events, directing the videos, being the on-camera host, editing, uploading, publishing to the web, and following up with the clients and handling customer service issues. I started to realize I needed to delegate and add people to my team so I could focus on the most important aspects of my business and really take it to the next level.

I started looking for interns. What a total life saver! I found a great marketing intern who could help with booking events and jobs, as well as assisting with our social media strategy. I found a few editors that I trusted to help edit some of our videos. Then I found an assistant to help me with all the other tasks I needed help with, the nitty gritty of the day-to-day. It really took our business to the next level and allowed me to focus on our goals as a company. I went through internships.com which was an amazing resource, posted job listings at local colleges, and also found people through social media!

Any final nuggets of wisdom to share with others who are joining the entrepreneurial ranks and recently launched or are thinking of launching their own business?

Stiletto Escape: “If it’s important you’ll find the time, if it’s not, you’ll find an excuse.” The initial lustre of owning your own business and pursuing your passion can wear off very quickly. It can become too easy to put things off, especially if you spend eight to 10 hours working at another job.

The Pulse: I would say DREAM BIG! You will get a lot of naysayers that will tell you can’t do it. I heard that several times, but I never gave up. Believe in yourself and your company. Never take no for an answer. If I took every “no” I got as the final word I would not be where I am today. You will fail at some point in some way, but just learn from that and pick yourself up and move forward.

Lastly, adapt to your clients needs and demands. Know who your target market is and listen to them. We made changes in our business and adapted to what our clients were asking for. It gives you longevity and helps you to stay on the cutting edge of your industry.

 

Jana, Shivani and Cindy—Thanks for taking the time to share your stories!