Cold Calling on the Couch to Multi-Million Dollar Business

Entrepreneur to Enterprise

Most entrepreneurs and agencies face the same problem: not knowing when it’s the right time to start expanding and scaling their services. Let’s ask ourselves a few questions.

  1. When do you start hiring more people?
  2. How do you scale your services and expand on what you offer?
  3. How do you restructure your company and how it operates?

Vendasta has gone through many levels of growth, every 6-8 months or so in fact. We have restructured the way we function as a team and as a company, what services we provide, scaling those services, adding new employees, and expanding into different services and verticals. We’ve been there. So have our Partners.

Just think of Vendasta as your super-wise big brother.


Entrepreneur: A person who organizes and operates a business. 1-2 employees.

Agency: A business with 3-99 employees.

Enterprise: A business with 100+ employees.

Why Expand? Why Grow?

Playing it safe is not a business strategy.

The “Play it Safe” mindset leads approximately 32 million American business owners to avoid risk entirely and suffer from smallness. - Nageen Riffat

An Agency playing it safe can lead to missed opportunities, not meeting the demands of clients, not having capacity for new clients, high employee turnover, and not being able to compete in a competitive market.

Entrepreneur to Agency - Social Ordeals

Social Ordeals started out as one guy eating chips on his couch while making cold calls out of the phone book. Now, they are a multi-million dollar business with several offices. At Vendasta, we consider them a Premium Agency.

Social Ordeals is a digital marketing agency that was created to offer real world solutions for real world problems. With over 25 years of Interactive Marketing, Social Ordeals was created out of the desire to offer small to midsize businesses real insight and real solutions that have been tested and proven to be successful.

They offer the following solutions:

  • Online Listings & Citations
  • Review Monitoring/Generation/Response
  • Social Media Marketing
  • SEO offline/online
  • Digital Advertising (Adwords/Retargeting/Display/Social)

We asked Chris Montgomery, CEO and founder of Social Ordeals—aka the guy eating chips from his couch— how he turned himself into the Premium Agency that Social Ordeals is today.

Chris Montgomery was gracious enough to let me pick his brain on how he scaled and expanded Social Ordeals.

The Goods

How many employees did you start with, and how many do you have today?

It was just me, a true entrepreneur, a serial entrepreneur—A serial entrepreneur is an entrepreneur who continuously comes up with new ideas and starts new businesses. Now, we have 25+ employees and we operate out of California.

How did you start growing?

Our first sale was in 2011. I had no experience in the digital market but I knew where the market was headed. Selling wasn’t anything that I wasn’t used to. There was no YEXT when I started, everything had to be done manually. We were completely immersed in the Vendasta Platform in 2013.

What did you find helped you grow faster?

Cold calling was my life, 98% of my leads came from cold calling. From that, it was referrals.

We would partner with website companies and refer clients to each other, we shared the love. We started giving away a month free for referrals, and it worked. We started building an online presence with 100+ stories on Google reviews. I found that it was better to not just be the salesperson, but to develop trust.

I was once challenged by a client, he asked how Social Ordeals was different. I explained that we were the unicorns, there were very few agencies in our area selling reputation management or digital. We established ourselves to be the trusted advisor and we weren’t greedy. Starting clients off with a package that made sense and starting them off with the foundational products. We now have clients that I haven’t spoken to in a year and they spend $2,000. They trust Social Ordeals as their digital rep, trust is everything.

What stunted your ability to grow?

Not having a web presence and not having those reviews. The reviews from our clients were so valuable. A digital agency today better be ready to roll up their sleeves and grind, they really need to understand what they’re selling and the market they are selling in.

Digital wasn’t really around when I began Social Ordeals, digital wasn’t seen as the place to be. I set clients’ expectations and was real. I was able to demonstrate and show the ROI with the value using the foundational products.

How has Vendasta helped Social Ordeals scale their services and expand the products you offer?

Continued support and growth. Vendasta is on the front line of the best technology that’s out there.

I look at my relationship with Vendasta as my personal technology company. Vendasta is always there to help. This software feels like my software, I feel like I am a part of the Vendasta team. It’s like having a tech person in our back pocket 24/7 to help myself or my clients with anything and everything that we may need.

How have you had to restructure departments as you’ve grown?

We have done and tried everything. From account managers, listing divisions, social divisions etc. I am still selling, not because I have to but because I love it. It’s really a trial and error thing. Finding out what works for the now and looking forward to the future.

Having the ability to be agile in allowing ourselves to always reorganize when it functionally makes sense. We have become that big boy agency, and bring all our services in house.

Tips for other entrepreneurs that are in the position you were in the beginning?

You have to start your agency off with personal relationships, not cold calling. Spend $5,000 or less in advertising, go after the low hanging fruit around you. Build those relationships around referrals.

About the Author

Colleen is the Content Producer at Vendasta. Her passions are marketing, equality, and blogging. She enjoys adventures in the mountains and in her hometown of YXE. You can often find her in a plant store or with her dog, Frank.

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