It’s time to highlight
another powerhouse in our growing industry! And my guest this week on The Confident OBM Spotlight is particularly near and dear to my heart. 

Let’s welcome Teresa Cleveland of The Entrepreneur’s Toolbox

I can’t help but be extra excited about this week’s interview, because Teresa and I have been thick as thieves for a while now. Back in the day, long before I started teaching the The OBM Certification, I coached Teresa as she built her OBM biz. She went on to get certified with me, and the rest is history.  

Let’s dive in! 

Sarah: Hey Teresa! I couldn’t be more excited to FINALLY be hosting you on The Confident OBM Spotlight. It’s about damn time! 

So for our audience out there who doesn’t know you as well as I do, tell us! How long have you been hustling in the online biz world?

Teresa: So excited to be here, Sarah! I’ve been at it for 13 years now – 3 years part-time, and 10 years full time! 

Sarah: That’s amazing, Teresa! You have quite a few years on me, actually!  

Tell me a little bit about your career journey before becoming an OBM. What was your trajectory?

Teresa: I’ve held a variety of jobs. And my favorite gig other than what I’m doing now was being a Property Manager. I’ve always been an entrepreneur at heart, even selling pot holders I made as a kid. I’ve started several businesses over my lifetime. But it seems as if I was always looking for the right fit. 

In the corporate world, I was always promoted quickly, sometimes over people who had been in the field longer. My daughter used to say that I could start working somewhere as a janitor and end up running the place. 🙂 

One of the downfalls of working for someone else, is that even if your ideas are more effective or efficient, it doesn’t mean they will be implemented. And you may have to continue doing things ineffectively and/or inefficiently. It may sound presumptuous, but I’m just not built to do that for very long. I finally decided that I was going to do my own thing, once and for all, and started really exploring what that meant. 

Sarah: I hear you and I couldn’t agree more! OBMs are incredibly efficient, systems-minded people. We don’t squander our energy, and want to make things “work” as quickly as possible. I also ran into that issue over and over again in corporate. The bureaucracy was always such a huge barrier to much-needed change! 

Did you work as a VA before you became an OBM? If so, how did that experience prepare you to hustle your ass into an OBM role?

Teresa: It’s interesting to look back! Because I always had an aversion to calling myself a VA. 

As I was exploring what I wanted to do, I tried a few things, each time learning everything it took to build an online presence for my endeavor. Before long, people were asking me how I did things and if I could teach them. Or, even better, do it for them.

I started building websites for others including for the certified facilitators of The Passion Test. I was obsessed with email marketing and creating campaigns and sales funnels, even before they were called that. I was doing more than just checking off tasks. I was actually helping other entrepreneurs see the whole picture and plan for it. 

I knew what I was doing ran deeper than the general VA services most VAs were offering back then. I just didn’t know what to call myself. I went through a lot of titles trying to define myself. It wasn’t until about a year and a half ago that I realized OBM was EXACTLY the right fit. 

Sarah: This is such a common narrative among participants in The OBM Certification! So many of us have hustled as OBMs in disguise for years, undervaluing our services and contributions to our clients. 

What was the tipping point that kicked your ass into high gear to uplevel your skills and services?

Teresa: Plain and simple: I knew that I wanted to work with clients who were further along in their journey than I had been working with.

Think you’re ready to scale-up your client base? Take the OBM Quiz to find out! 

As an OBM, are you a generalist or specialist in a certain set of skills? And why do you prefer that?

Teresa: I’m a generalist. I thrive on the diversity of challenges and projects that come with being a generalist. 

How has the freedom to work from home impacted your personal life?

Teresa: It has ruined me. LOL! I don’t think I could ever work a traditional job again. I mean if I had to, of course, I would.  

Just this year I was able to spend the month of February in Coronado, California. Believe me, that’s huge for a girl that lives in Ohio. By February, we are so over the cold, gray days! I packed up my 5 year old and off we went. I worked part-time throughout the month because my amazing team had my back (and my clients) covered. In my day-to-day life, I have peace of mind, joy, and happiness personally and professionally. 

Sarah: It’s ruined me as well! I’m a mama to three kiddos, and I live thousands of miles away from my family. I don’t think I could function in a traditional job anymore, without the freedom to rearrange my day for a sick child or the occasional trip back to Canada to visit the fam! 

What are the kinds of tasks for clients that get you excited to start your work day? Any tasks that just really aren’t your jam?

Teresa: I love creating systems and flows but I hate maintaining them. I love the relationships I have with my clients and my team. 

How do you organize your day to keep yourself efficient and accountable to your clients while still enjoying the perks of a laptop lifestyle?

Teresa: I set certain days/time frames for different types of activities like calls with clients, sales calls, team meetings, etc. Teamwork PM has also been a huge help in this area. It helps us batch work. 

Client boundaries. How do you set them with your clients to provide a high level of service that doesn’t cross the line into consistently over delivering?

Teresa: I make sure our services/deliverables are outlined in our consulting agreement and I also reiterate and set expectations in our kick off call. It makes it much easier to say things like “I think that’s a great idea. Would you like for me to have Kassie put a quote together to add that to our current agreement?”

What do you do to attract new clients?

Teresa: The clients I already have, reaching out to past clients for referrals, building a strong network that sends prospects my way, having a presence in appropriate FB groups, and attending local networking groups.

What advice would you give to other aspiring OBMs who are considering this transition?

Teresa: Buckle up, Buttercup! If you’re committed to this transition, you’re in for an exciting and fulfilling ride. Document your procedures, build strong relationships, and align yourself with mentors and leaders that resonate with you. Be forewarned that there is quite a bit of self-development in this journey and it’s worth every minute!! (Tweet it!)

To get in touch with Teresa, visit her at The Entrepreneur’s Toolbox and connect with her on Facebook.

Now over to you: Are you an OBM in disguise? What’s holding you back from stepping up? Tell me all about it in the comments below – I love to hear from you!


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