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Jess Columbo


Jess Columbo

Gabriel Flores  0:00  

Hello, everyone, and welcome to the shades of entrepreneurship. This is your host, Mr. Gabriel Flores. Today I am here with the owner, Jessica Colombo of tiller. I'm very excited about this one because I actually worked with this individual for so long. And then I've actually got to see this individual progress into this into this, you know, entrepreneurship role. So, Jess, how are we doing?

Jess Columbo  0:26  

I'm as good as I can be. Yeah, but I'm no, I'm totally delighted to be here with you. Thanks for having me.

Gabriel Flores  0:35  

No, I'm excited. I'm really excited. Because as I was mentioning earlier, you know, you and I have known each other for years, we've worked, you know, just literally next door to each other in the same office in corporate America for some time. And I, you know, I'm really excited about this story. Because you you may work in corporate America, you were, you know, very, you're rising pretty quickly in the ranks. And then you said, you know, I want to start my own thing. Now, before we get into all that. Let's introduce the world to Jess Colombo. Cool, okay, gets a little background.

Jess Columbo  1:07  

Okay. All right. Oh, my God. Okay, I'll try to, but my motto was be brief, be brief, be bright, be gone. So that's what I'm gonna try to do. Let's see graduate, I was a poetry major, much to my parents disappointment at a very expensive liberal arts college, and came out and said, I want to write for a living, which sounded pretty cuckoo, and actually gotten in touch with a staffing firm here in Portland, and said, Hey, can you stick me in any business that will have me if they pay me to write, and they put me at a really phenomenal, supportive boutique PR agency, and I had never gone to school for PR, I didn't really have an understanding of what that looks like. But it was right at the kind of upward slope of social. So I was there, as Facebook opened up from college kids to brands and Twitter kind of came online. And as the youngest kid at a creative agency, I had the opportunity and the trust from leadership to say, Hey, I think there's something to this, and we should check it out. And can I play in the space and start selling it to clients. So about 15 years ago, now, I started doing social for brands that were really mission driven. And then 15 years later, I have this kind of a unique privilege of doing that on my own, but lots of twists and turns along the way. I've been agency side and in house, large organizations and smaller ones. And I think the the thread maybe is somebody recently was working on a rebrand for me. And she said, I think you're the Brene Brown of digital marketing. And I totally cringed at that and then also felt absolutely, you know, humbled and, and, and flattered by it. But I think my background is, is around to, let's say, even edit some of themselves. But but I'm interested in the internet being still, at this point in its evolution, a place for good, a place to connect human beings to other human beings. So that's what I get to do now. And I'm really grateful for it.

Gabriel Flores  3:25  

Talk a little bit about what it is you do now, what? What is tiller? What does it do?

Jess Columbo  3:31  

Yes. American is as to how to use social and digital platforms to connect humans and tell really great stories. And Tiller still get to do that. I say I accidentally built the agency, the marketing and communications agency that is killer, because that wasn't necessarily my explicit intention. When I left corporate, I said, I know I want to do this. And then I was just really lucky to have clients say, we not only are buying kind of what you're selling, but we want you to do it for us. And at the time when I was trying to pay a mortgage, and and kind of get my footing. I also had a lot of really talented people around me, who could do kind of complementary services and can do a lot of the execution. So six years later, I have an agency and we do marketing and communications for regulated industries. So I would say 70% of our clientele is healthcare, but also higher ed and government, nonprofit, financial services and cannabis every once in a while when we get a grown up client and that space. But marketing communications, a lot of it is focused in the digital social space. And then over the last few years, we've really built a book of business on the crisis. And to so supporting executives and teams as they show up and try to support their own employees but also how we de escalate Wait and manage really tricky stuff that's happening across the internet. So I jokingly say that as a consultant, I help people not get sued for silly things they say, online.

keeps it interesting. Yeah. Oh my goodness, we've been busy. I don't know, I

Gabriel Flores  5:22  

think some people probably need that a little bit more than others, I'm sure.

People at home during this pandemic, man, we got Twitter fingers, we got much to do. So let's talk about how the concept kind of created a started a little bit because you mentioned you were in corporate America and decided to leave. So I want to do

Jess Columbo  5:46  

where I am now. Because it opens up a larger kind of give yourself permission to change course, anytime, for any reason. If as you're building your practice, you realize that it isn't adding to your life in terms of kind of your joy, or your finances or your the time you get to spend with the people that you care about, or the types of work that you want to dig into or the strength of your professional services, then get to change course, but I didn't give myself a lot of permission. And I, I would tell you know entrepreneurs to do that and get really worried about your elevator pitch, where I'm going to tell people, This is what I do and why I do it and how I do it. And then life changes in the world changes, and you might want to go back in house, or you might want to do something else. So when I left corporate, I had was in a position after a number of years of building, there were my kind of values and the work that I wanted to do wasn't necessarily aligned with, you know, the structure and the people that were in place anymore. And so I had a really unique gift, where I was able to go halftime at corporate, so I powered down but I still had income, I still had benefits. And I started to go identify some independent clients that I could bring on. So I was I was still able to, you know, subsidize my household while I went and built the practice, but I thought I was going to leave corporate and do continuing school education training, CMA training for healthcare providers on social and digital, I knew that there was this really interesting intersection of ethics, and kind of professional ethics, and online. And a lot of folks were aching for that kind of education. And I was able to build that when I was in house with some organizations, and I thought, Okay, I'm gonna go out there, and I don't have to go get that business, right, our clinical providers, or doctors or nurses or pharmacists, they all need to get continuing medical education credits. So there's my sales pipeline, I'll just go and get accredited. To do that, I'll have the material and education training materials to do that. I started doing informational interviews with people and realize what the upfront cost of that would be. And kind of the logistics of setting up that kind of service offering. And it was I couldn't afford to do it. So I started taking stuff that people knew me for that, which was really social media strategy, and social consulting and things like that. thinking, Oh, I'll get back to that. I'll get back to that. But I named my my, the first iteration of the business med Ed digital, I was doing medical education, specific to the digital space. Okay, first of all, to total, like mouthful, nobody likes that that's not a good, it's like, it's such so much. Like, what a beautiful thing, you know, like try it and fall on your face and try something else. And so there was there's been a lot of pivoting and and in the six years. Then we launched tiller, maybe four years ago as a separate practice altogether. So as the legalization of cannabis was kind of coming to pass here in the Northwest, I've got a lot of personal values alignment with addressing the opioid epidemic. And we were seeing that every state that was legalizing saw an organic drop in opioid use, and thought, Oh, it's this is something that's aligned with our values. Let's go get it. But as soon as I started taking on cannabis plants, even really mission driven, you know, public health oriented campaigns, like health care and other regulated clients got nervous. And they said, we're uncomfortable being associated with that. And so I had to, I had to launch a separate practice altogether, which tiller. Now, a few years later, they're interesting, you know, kind of socially, culturally, everything has evolved to a place where we can be one practice that everybody can be under one roof. Interesting. Yeah, it's been a ride.

Gabriel Flores  9:45  

You know, other organizations, obviously. Interesting. That's, that's kind of, yeah, that's kind of interesting to how you know, other organizations. Obviously, they feel like you know, they're creating this partnership with you right to create your content. And so your affiliations is also looked at what very interesting for, you know, small business owners to think about as well, you know, you mentioned to, you kind of work with a lot of providers from a CME education. So for those at home CME stands for Continuing Medical Education, and these providers needed on an annual basis, you know, some need, surgeons need a specific amount of hours versus general practice. Now, you mentioned, because a lot of there's a lot of providers and a lot of just normal people in general, just everybody's on the internet, right? What is, and you kind of mentioned you, you teach them on some ethics, what are what are some nuggets that some folks maybe let some things off, that's

Jess Columbo  10:40  

been kind of in the practice, as we've, you know, shifted and taken and launched new arms of the business, and I've done consulting, in addition to agency management, the teaching is my favorite favorite thing. Because when you're teaching, you're also learning and in the last two years, the things that I was teaching and kind of painting on from clinical education, of, here's the opportunity of being in the social space for you to connect with patients, for you to do continuing education to, for you to understand the patient's, you know, psychographics of who you're serving for you to continue to find research, collaboration, all these phenomenal opportunities of clinical professionals being in the social and digital space, when COVID hit, the stakes became just astronomically higher, and you've a lot of risk that wasn't there. And there was a ton of risk before. And that's what I would, I would teach, here's how we can, I can empower you to engage safely in this space. So if you're really confident to go do that, and, and then inherently, it creates the table for the institution that you work out, right, if I've got all my subject matter experts going and doing really great work publicly, I can do less billboards for the hospital. But when COVID hit, there was a there's one example of a provider, a public health professional, who made the YouTube video where he was wiping down his groceries at the very beginning of the pandemic. And I think he was out of MIT or another East Coast institution. Well, because of the iterative nature of science. And this is what kind of collectively people don't understand about what's happening with COVID, and Fauci and everything else, that science is iterative. And so public health protocol is also iterative. So the things that we were teaching at the beginning, we have since come to understand better and differently. And so the public health protocol has evolved. So the guy who was wiping down his groceries, puts it on YouTube, and does this really great public health education piece, it goes viral, in the meantime, we've learned more about the disease, to know that you don't have to wipe down your groceries. And in the meantime, that video went viral, and he can't take it down, and he can't stop it. And he now is putting out public health education that isn't on point with the current protocol. Right. And he will mentioned that in an article I was reading, and that risk, or of being lambasted by colleagues, or by patients, or, you know, where is the line of libel and slander and defamation, and that's where we walk together and where I support a lot of folks as how do we get out there, but but position you in a way that, that you feel really confident? And then how do we empower you with the tool so that you understand, understand where the boundaries are and how to de escalate issues, because, unfortunately, clients is under attack. And, and the democratization of information and dialogue that is the wonderful about the internet, also had has a dark side. And I think we've all been privy to that, especially in the last couple years.

Gabriel Flores  13:50  

That's some great takeaways, especially for society as it is now. Yeah, that's, that's some great takeaways, especially for society as it is now. We're very much like, we want to be the first right, we want to be the first to break the news. We want to be the first out Yeah, but it's also important to ensure that the information you're sharing is accurate. It's, it's so important that this information is accurate. And it's it's not harmful to others, especially if it's inaccurate information, because too often inaccurate information can be harmful to others, whether it's, you know, an individual themselves or a culture or community or, you know, generalization of an entire society. Right, there's just too much right to your point. Greatness, right? Right. And difference between slander and defamation are very much and there is very much of a very out of

Jess Columbo  14:49  

your control, but it's really important to consider around the context of the delivery of that message and and yeah, yeah, I had another example in my head as you were describing that which was back in the day in corporate hospital systems, the other one would be, and more important than ever, least more visible. And finally, more invested in is the idea of kind of equity in your messaging. And when you said, you know, everybody's on the internet, and I would have said, Yes, two years ago, and in the last two years, Tiller has done more out of home marketing than we've ever had to do from an equity standpoint. So two, three years ago, we were putting out social media commentary that said, hey, decrease your corn intake. And you know, it shouldn't be a big part of your diet. What does that mean for the Hispanic population? And what you know, in other Latin communities were like, culturally indigenous communities. Or we would say, Hey, don't show a picture, when you go on, I have an older white male doctor leaning over a person of color, giving them some chronic condition methods, right, that really looks punitive. And looks like there's this really explicit power dynamic shown in that visual, it's on a totally different level. And now if I need to reach my historically marginalized community who doesn't have access to the same information, or health literacy level, or who needs things in different languages, or who has to keep going to work, when the rest of us get to stay home, then I need to start doing transit ads that have Spanish translation. It's just, it's a totally different game. And it's a totally different consideration. Even if we're talking about kind of digital communications on how we show up for people. It's different, and thankfully, I guess it keeps me employed.

Gabriel Flores  16:37  

Yeah, because you know, this is a business, right? Yeah. So let's, let's talk about the employment piece, because you know, this is a business, right? How did you fund this business? How did you start the fund? And there's this grassroots effort? And I would say, they just kind of start getting going, Oh, clients. And so how did you get squirreling away

Jess Columbo  16:59  

dollars as much as I could, and cutting costs in my own kind of home space? Okay, I don't need to eat out, and I don't need to buy that thing. And then I mentioned I went halftime, so I continued to have income and benefits, which was huge for me at the time. But the huge out of pocket that you're not thinking about is your retirement contribution. And your health care when you walk away, especially if you are a provider of others. Holy crap. Oh, my gosh, and I'm a

Gabriel Flores  17:30  

health care costs. It's expensive.

Jess Columbo  17:35  

Aging in America or Dying in America, I think about it every day. So the idea of leaving my corporate gig and not continuing to contribute to a retirement fund of some sort, even if it's just a piggy bank, was a non negotiable for me. So I had to figure out that in my budget, so doing that budget rundown, and just knowing your numbers is pretty paramount when you're going to walk. So I did that. And then and mentioned, I was able for six months as I launched the business, kept healthcare and kept some semblance of a salary coming in. And then I had one client when I came off, and it was kind of an ongoing, it was a three month kind of training. But going from a one off project to a retainer, like getting that first retainer client, because you are always grinding for the next month or the next quarter or the next something, you've always got to have your pipeline filled. And, and that was a really scary endeavor, the first kind of walk, you feel like this precipice that you're going to just get off the cliff. But also, if you've got the energy and the drive and the passion in your belly to even consider the step, then you know that after that step, you're going to keep grinding. Right? Like, I think it's a lot of a lot more mental toughness than anything else.

Gabriel Flores  18:57  

Yeah, totally, totally. You mentioned to this kind of isn't your first business because you basically pivoted? Yeah, I like it. Man, you know, you mentioned to this kind of isn't your first business because you basically pivoted.

Jess Columbo  19:13  

We have together what we'll try to I think I mentioned that kind of giving yourself permission to change course when it's not working. And I didn't pull out when I had launched Tiller originally, and we were designed to be an agency that an arm of the agency that that supported cannabis clients, I was getting small, low budget clients that were really mission aligned that cared a lot about the industry and the planet and the people and then I was getting really high budget clients who were jerks. And that didn't align with my values. And and I tried to push that mountain that that ball up the hill for longer than I should have. I should have pulled the pulled out earlier, I should have pivoted earlier. But I You don't know until you're in it. And so every time I get better and I start to smell food, this is actually kind of a loss leader for me. Or, Yeah, this isn't. You look around one day anything, I'm doing it and it's working. But are you happy? Is this feel good? Does it feel are you continually moving into more alignment with the person that you want to be in the world, and not in a cheesy way. So I would tell you, I haven't taken care of myself physically. And it is a really physically demanding endeavor. And I had some health issues over the last six years, just because instead of taking time off to go for a run, or stepping away from a computer to drink water, I have been physically carrying the business for a while, work longer and harder, and not take time off and not take care of myself, or meditate or do yoga, or hang out with your friends. And the business will not work if you don't like you don't work. And so I would just say, continually, it's going to be a work in progress, but continually getting your permission, give yourself permission to change course, when it doesn't feel right or not working and pull the plug. And that doesn't mean that you failed, it means that you're working smart, for Sandra and green brave enough to say actually, I'm going to do something different now. And then really investing in your physical health. I think I took that for granted at the beginning.

Gabriel Flores  21:42  

Yeah. Do you feel like there's any having the previous experience in corporate America? Nice. Now, do you feel like there's any having the previous experience in corporate America? None of that? Do you feel that there was no easy points kind of transition.

Jess Columbo  22:01  

Not that it's a good or a bad thing, necessarily. But I've been 100% referral base. And that means that sometimes I get referrals of work that aren't really in my wheelhouse. But I've never gone to get in business and never had to think because I worked my tail off that relationship development and this town of a small one and this town being Portland or the Northwest or you know where you've worked before. And then those people go on to other organizations and think of you, they're there. And I think that's been really organic for me that I've cared pretty deeply about people. And then that has, that's benefited the business quite a bit. So I don't, my new business is talking to people like you and make sure that I'm paying attention. When you say on LinkedIn, hey, I'm looking for this, that I think about my network and look for ways to help you. That's what my new business strategy is. And that feels really good.

Gabriel Flores  23:05  

Yeah, now, you mentioned you know, you've kind of love it. I love it. I mentioned you went through a health scare. I love it. Yeah. And now, you mentioned you know, you've kind of gone through like pivoted you haven't you kind of mentioned you went through a bit of a health scare recently, last couple of years? Because you've been so devoted on AI? What What advice would you give yourself? Would you change anything, what did jokingly

Jess Columbo  23:28  

but absolutely not to do is to get yourself in great there. I've been through a couple of different therapists in the process. And they've all helped me at different points in the journey. But for a while I was working with somebody, I was looking for a business coach for a long time and had a lot of trouble finding somebody that was a good fit for me. I had, you know, I guess, generally speaking, I had older white men telling me how to run my business. And it felt like oh, I'm not sure you really understand the nuance and the complexity of what I'm up against as a woman. And then I had some others that were really more woowoo. And I wasn't in a place where I wanted to hold hands and talk about things. I really wanted to go get it I'm a hunter by nature, on the field person by nature. And so it was really tricky to find myself somebody that that could support me and inspire me in that way. And I actually found a therapist who specialize in working with entrepreneurs, and I was able to pull apart you know, your scarcity versus abundance mentality and to roll around in the dirt of like, what money equals to you because you are in the thick of how your value and your income align and what your value proposition is in the world. And if you don't have the same amount of money coming in every how that makes you feel unsafe. I mean, those are some do Deep rooted things. And so somebody who just kind of was able to work through that, or allow me to talk through that was really, really helpful. And it can be a really isolating experience. At the end of the day, the buck stops with you. And if you're unhappy, or if you're happy, both of those things are your responsibility. And that is a totally freeing in the best moment, I feel most free by that, right, I'm clocking in I don't have somebody micromanaging me. And when I'm miserable, that's my responsibility, too. And so having a support system of your personal group, but also a trusted Small Business accountant, a trusted mental health professional, you know, some of those other kind of professional services were really important to me along the way.

Gabriel Flores  25:49  

Know, you've been in this industry, you know, individually as a, you know, sole proprietor, entrepreneur. Nice. Now, you've you've been in this industry, you know, individually as a, you know, sole proprietor, entrepreneur for the last six years, you mentioned it, but you've been in it for even more than a decade, almost coming on two decades. What advice would you have for individuals in the, in the same industry of yours,

Jess Columbo  26:15  

kind of base level community over competition, and I was just reading something from a Seth Godin piece that you could have, you could see a really full area or marketplace. And you could see, wow, there's tons of consultants and businesses in this space. And you could see that and say, It's too crowded, there's no room for me, or you could see it and say, Wow, there must be a lot of need in that space, there must be a lot of opportunity in that space, right? If there's so many people building building practices. That's what I see, when I look at our space, I see a lot of people who say they do what I do. I know nobody does, what I do the way that I do it, because people buy my brain at heart, they don't buy my Facebook. And as a consultant, I had a mentor told me, you know, I'm often I'm always certain, and I'm often right. When a client buys a consultant, they, my job is to walk with them and to make them feel safe. And I don't have to be right all the time. But on the right a lot of times, and and that's why I feel you know, like I have business being in this space. But I would just say that there's more than enough room for all of us. And explicitly, if you are a person of color, if you're a woman, if you're a person than any other historically marginalized group, you should increase your pricing by 20%. That's what I would tell you, because you're not asking for it. And I interview and I work with people who maybe are more privileged. And they ask for it, and they get it. So I just wouldn't say charge more. And go get it because there's room for everybody. And there's really good work that needs to be done and a lot of people that need your help.

Gabriel Flores  28:12  

Community over competition. That's that's Oh, yeah. Good. Yay. I like it. I like the community over competition. That's that's a, that's a quote right there, baby. I'm gonna use that one for a while I run with that. I like it. Thank you so much for coming on first and foremost. But for the folks at home that are interested in learning more about working with you on

Jess Columbo  28:38  

the show, I love to hang out and learn and connect with people. So Jeff Colombo, on LinkedIn, Twitter is another place where I love to get into conversation with folks. And then Jeff is probably I'm launching a whole new iteration of my brand in the new year. Please invest in your own brand, everybody. And if you need hookups for that I've got great creative people in my network, but just it's probably the best place to get to me.

Gabriel Flores  29:03  

Yes. Thank you so much again for coming on the show. Thank you.

Jess Columbo  29:06  

Oh, my gosh.

Gabriel Flores  29:10  

Perfect. Just thank you so much, again, for coming on the show sharing your story, a lot of informative information. I think a lot of people will find a lot of value out of this one because I think this adds a lot of value added to I'm very excited to actually be able to share it. Thank you again for coming on. I'm looking forward to your hopefully some future work and projects together as well. But those folks at home please visit me on the Twitter, Instagram, Facebook or LinkedIn. Thank you and have a great night. 

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