From Employee #1 To Owner – Daria Grastara (Direct Persuasion)

Eric Wilson
June 12, 2024
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From Employee #1 To Owner – Daria Grastara (Direct Persuasion)
June 12, 2024

From Employee #1 To Owner – Daria Grastara (Direct Persuasion)

"It matters more who you work for and who you work with than where you work or what your title is."

Daria Grastara is CEO of Direct Persuasion, a performance marketing and persuasion advertising agency serving Republican campaigns and issue advocacy organizations. During the 2022 election cycle Daria was Digital Director at the NRSC and she’s also worked on the Trump campaign and at the NRCC.

In our conversation, we discuss the transition in ownership of the firm, that challenges she’s faced as an entrepreneur, and the lessons learned along the way.

Episode Transcript

Eric Wilson (00:33.294)
I'm Eric Wilson, managing partner of Startup Caucus, the home of campaign tech innovation on the right. Welcome to the Business of Politics Show. On this podcast, you're joining in on a conversation with entrepreneurs, operatives, and experts who make professional politics happen. Our guest today is Darya Gristara, CEO of Direct Persuasion, a performance marketing and persuasion advertising agency.

serving Republican campaigns, committees, and issue advocacy organizations. During the 2022 election cycle, Daria was digital director at the NRSC, and she's also worked on the Trump campaign and at the NRCC. In our conversation, we discussed the transition in ownership of the firm, what challenges she's faced as an entrepreneur, and the lessons learned along the way. Daria, you started out as employee number one.

at Direct Persuasion in 2018 with founder Gary Coby, friend of the pod. What did you see in the firm then that that got you on board?

Daria Grastara (01:41.678)
Yeah, I always set in the beginning of my career, I don't do this anymore. I always set goals one cycle ahead. So in 2016, I said, what do I want to do in 2018? Let me make sure I get all those skills now so that I can be qualified for that job in 2018. And when I was finishing up the 16 cycle, I was on Jeb Bush.

Eric Wilson (02:01.582)
Sorry, I just want to pause you right there, Dariette, because that's really good advice. Anyone who's thinking about building their career in politics. I just want to park there real quick. How do you think about mapping out those skills? Are you reverse engineering where you want to be and who has those skills?

Daria Grastara (02:22.446)
I think looking back on it now, I can give you a more like in -depth analytical approach. I think I chased job titles early in my career and places. And I always tell my team now who cares where you work, what your job title is, follow the boss. Like whoever you're directly reporting to will have such an impact on your career more than the name on the resume. and so, but back then I did not care about that. So I think I was chasing places and I was chasing,

Eric Wilson (02:31.214)

Daria Grastara (02:52.302)
Like I was trying to level up and I think I was spoiled with my first job being Jeb Bush's presidential because I got that little taste of what a presidential campaign could be like early in my career. And then I just wanted to work on big scale operations. And, and so after I finished six. Yeah.

Eric Wilson (03:07.79)
All right, so I'll let you get back to how you got started at direct persuasion, but that was just really good advice. And I wanted to make sure everybody paid attention to it.

Daria Grastara (03:18.254)
Yeah, and I think too on that note, I always advocate for learning the hard skills early in your career and trying to get that done because you can't be a 30 year old operative who doesn't know how to mock up an email and who has never, you know, managed an email program. And so I always advocate for that. And I kind of, I learned a lot of hard skills very quickly in my career working on Jeb. And then I went to FP1 and I was one of the...

first few digital people there building out that digital operation. I wanted to chase bigger scale in a national operation. And so I was watching Trump 2016 on the sidelines and I had a lot of FOMO, wanted to be part of it. And I knew I wanted to be part of Trump 2020. And so when I was looking at how will I be looked at as a more senior level digital person for 20, I need to go manage a big budget, which brought me to the NRCC.

and managing texting there and building out a CRM and helping with all those special projects on a national fundraising level and not just small clients or down ballot races. So I knew Gary Coby was probably the man I needed to impress and I needed to get to know. And I didn't know what Derek persuasion was. I didn't know how he was involved with the Trump campaign. I just knew he was highly respected and very smart.

So when the direct persuasion offer came and I knew I could be reporting directly to Gary and helping him with a startup, I said yes. I had no idea the other opportunities that would come with it and what direct persuasion would then bring me. So Gary is a performance marketing genius and I got to learn that very, very quickly under him. And then he actually partnered with someone on the corporate side who taught me a lot about

a corporate marketing machine that I would never get exposure to in DC. So like forecasting and QBRs with clients and setting goals and hitting goals and making sure to reiterate those goals over and over with clients. And also the soft skills of like having one -on -ones with a boss and having one -on -ones with your junior and that corporate consistency that DC lacks severely.

Daria Grastara (05:37.134)
And then also just building a vertical from scratch. But I would say when I was, the negotiation with Gary was hilarious for me to join direct persuasion. And like you said, I was employee number one. We negotiated my salary over text. He turned over an offer within 24 hours. I told him I needed healthcare. And he was like, you're the first person to ask that. Sure, I'll get on it. And I saw how quickly he moved. And it was like, Gary,

to me at that point in my career equaled like super low ego, but extremely high stakes. And then he just had tremendous trust. And I never had that before. There's always something in that recipe missing. And yeah, it just, it made sense and it clicked very quickly. And I'm so grateful.

Eric Wilson (06:27.022)
Yeah. And so earlier this year, Gary sold the firm, which is not that uncommon in our business, but what makes direct persuasion unique is that it's now employee owned. How did this come about?

Daria Grastara (06:39.406)
Yeah, I'm very lucky. Gary approached me about it. I was wrapping up the 2022 cycle as digital director at the NRC. I was weighing a bunch of options of what to do next. And he came to me with the offer and we didn't negotiate. It was a very simple process between us. He wanted to clear his plate and focus on more software operations. And he was trying to, you know, he was selling the corporate side.

of the advertising firm, he merged his texting tools and DP to him was kind of the last step. He didn't want to run it, but he has always made it known and always appreciated the fact that DP had a lot of high achievers inside who could run it. And he saw that in us before I think we saw it in ourselves. And it was really feasible and easy to hand off to us. And he was confident. We knew how to grow it.

And I'll use his words that he told me at the time. And he said, it would be very fulfilling for my career to see this new group of owners succeed. And yeah, I mean, yeah, it worked out. I had to get the other owners on board, but that didn't take much convincing either.

Eric Wilson (07:56.334)
So what are the early benefits you've noticed with this shared ownership structure?

Daria Grastara (08:02.734)
Yeah, Gary set it up in a really great way for us. So it was seller financing, zero interest. So that was the number one early benefit. It was way less intimidating. I knew we could achieve it in a cycle or less paying it off. But as far as benefits with the structure that we ended up putting in place, which is a group of owners who've been there since 2019, 2020, and then profit sharing for the rest of the team, employee retention.

is insane and an increase because what we offer is so rare. And I remember starting out in politics, you're just a cog in the machine and you're just an employee. They know who's going to be there for a year or two, and then you're going to switch a job. And I saw because of my team's experience and their relationships in the industry, they get poached very, very often by clients, by vendors, by competitors. And this has been the easiest way to prevent that.

because what we're offering is unique. And I would say number two thing is that the team has stepped up like never before. And I've seen tremendous professional and personal growth in the last year because I think it all clicked last year. Like, OK, we're betting on ourselves. And I noticed one little small example is that my team started reaching out to their networks that were always there and started selling and representing.

Eric Wilson (09:29.134)
They're now motivated.

Daria Grastara (09:31.182)
Yes, yes. And like they could have always done that, but they didn't until they had financial stake in it. So they went from like these doers to these sellers and strategists and owner mindset where they're charting their own.

Eric Wilson (09:44.494)
That's really fascinating. I think it's also a clear path forward because as you point out, the turnover can be really high in our industry. We are on this kind of two year cycle. But also the barriers to starting your own thing are so low now that I think incumbent firms are going to see, you know, it's not unlikely that you're going to see one of your star employees go off and start their own thing.

But if you align the incentives properly with this kind of ownership structure, to your point, give them that ownership mindset and really do more together than just constantly going out and undercutting each other.

Daria Grastara (10:32.014)
Yeah, it's a revolving door in DC. It's exhausting for everyone involved. And so to know that I have a team that's really in it and wants to help me build this thing, it's peace of mind. And I'm excited for them too. And I hope they see the upside and they see the opportunity here and realize that anywhere else is just like a short -term little dopamine boost for their ego. Here is something where...

Eric Wilson (10:58.894)

Daria Grastara (11:01.038)
It's longevity.

Eric Wilson (11:02.862)
And so this is something that you're going to pursue as the firm grows. You mentioned profit sharing. Is that something that you're gonna make a part of ongoing hires?

Daria Grastara (11:13.903)
Yeah, we're not offering it off the bat right now. I think trial periods are important to make sure it's a good fit for everyone, but we do talk about it in interviews. And it's been a great way to attract self -starters and like the live to work type people and weed out the work to live people. And we, I've always expressed the like work hard, play hard, startup mentality of direct persuasion in interviews.

Eric Wilson (11:19.214)

Daria Grastara (11:38.254)
But this has been like a great way. I always try to move very quickly when we do offers because I noticed that when I was hiring places, like how quickly Gary turned around an offer for me was something that was very appealing to me because it showed a lot about the company and the business and how quickly they can move on other things if there's problems, if there's client opportunities. So I think it helps with attracting the type of personality that I want to work around.

And then it just like also shows agility that we can offer this at any point. And there's not this like crazy board of directors that we have to get sign off on or these owners that are trying to maintain a lifestyle business. And so they're very greedy with the equity. Yeah, I want the incentives between the client, the owners and the team to always be aligned. And so when we're structuring deals, when we're hiring new people, when we're growing the leadership team, I want that all to fit in and this is a great way to do it.

Eric Wilson (12:37.326)
You're listening to the Business of Politics show. I'm speaking with Daria Gristara, CEO of Direct Persuasion. Daria, you touched on this a little bit, but an easier, possibly less risky approach would have been to start your own agency. Why did you decide to stick with Direct Persuasion and pursue this transaction?

Daria Grastara (13:04.142)
Yeah, I think three reasons that come to mind. One is the team. It would have felt, the team at Direct Persuasion is very special. I helped build a lot of it. And then when I was gone at the NRC, it continued under different leadership and was just as amazing. And I wanted to work with them. And like that advice that I said at the top, it matters more who you work for and who you work with than where you work.

and what your title is, like that matters so much to me. We have to do eight to 12 hours of this every day. Like I want to work with people I respect and trust. So the team was the big thing. I didn't want to have to start my own thing, poach from Gary. That made no sense. Which I guess brings me to my second one, which is loyalty to Gary. He opened so many doors for me and gave me opportunities of a lifetime and career highlights that I'll remember forever. And DP is his legacy too.

And so knowing that he could hand it off and it'll be in good hands and represent him well was important to me. And then my last thing, I didn't have words to articulate this at the time because I definitely got this question from family and other friends in the space. But David Seawright introduced Shout Out GP3. He gave me advice when I first told him this was happening to read the Seven Powers book. And I know Eric, we've talked about it too.

Eric Wilson (14:22.126)
Ha ha.

Eric Wilson (14:30.382)
Right. It's a must read.

Daria Grastara (14:30.766)
it's an amazing book. Yes. A must read. It's not super applicable. It's more for product companies, but I was able to morph some of the seven powers into a service based business. but DP has a cornered resource that I knew of, the, the industry knows of, with the experience, the portfolio, the learnings, like the raw numbers of learnings that we can use as benchmarks.

and the process power that we got from the crazy scale that we've operated at. I couldn't.

Eric Wilson (15:05.134)
You're talking about the past data that you have from working on Trump campaign, other really big races.

Daria Grastara (15:11.886)
Yeah, and vendor relationships and ad accounts and negotiations and deals that we set up. And I couldn't replicate that on my own starting out. And I think the cornered resource was a big one, but also the process power, which is another seven powers. Like Gary built a back office between all the shared companies where we had an amazing lawyer with reduced fees because a bunch of companies were paying him.

we had an amazing CFO and team that we was fractional that we could all tap into. And I wanted to utilize that and not have to spend any minute building the back of the business. I want to spend every minute building the front and doing the actual work.

Eric Wilson (15:54.286)

Eric Wilson (15:59.566)
All right. Have there, have there been any challenges transitioning the company after the founder's exit? And if so, how are you working to overcome those?

Daria Grastara (16:08.558)
Yeah, I think I felt this at a really small scale when I went to the NRC as digital director. I was like, no one here in this building is smarter at digital that I can learn from. Like it's the buck stops at me and I can't grow digitally. I'm going to grow soft skills wise, but I need to tap into an outside network to help me stay fresh on digital. and now this is that times a hundred with running a business. Like I don't.

Eric Wilson (16:21.806)
He he.

Daria Grastara (16:37.102)
have mentorship anymore in the same way I used to, in that I have to be the one to solve the problems. And so I've been making a very conscious effort to build a network around me where I don't know what I don't know. I want to have low ego with it and just help. And like, when have you failed? Or when we were creating the operating agreement, I just called a bunch of friends and allies in this space. And I said, what do you wish was in your operating agreement that you didn't?

Eric Wilson (17:04.526)

Daria Grastara (17:04.686)
And they all had like funny clauses that they would call it. and they're like, we added this years later. I should have done this from the start. This would have saved me so many headaches or so much money or whatever it was. so mentorship is a big one that I've had to build on my own and make sure I'm constantly seeking out because I never want to plateau or I never want to believe I know it all. because I feel very lucky being like a later to digital. Like I look at.

you guys and you and Zach Moffat and Chris Georgia and all these people who were at the very start of digital. And I got to the Lude Arts, Becky Donatelli even, who got to like build this all before me and I get to watch it and see how it succeeded, how it failed and learn from it. And so I want to keep that learning going.

Eric Wilson (17:44.686)
Mm -hmm.

Eric Wilson (17:57.294)
Yeah. When the mint, when the mentorship or the, that relationship isn't built into your structure, you do have to make the effort to go out and, and do that. I, I, I like the model. You may have read this before about, the personal board of directors, right? I'm thinking about like, you don't have a board for your company, but you can have a board for your, your career and doesn't have to be anything super formal, but it sounds like you've, you've assembled that. and, and that.

Daria Grastara (18:14.382)

Eric Wilson (18:27.406)
is obviously quite the transition because you built your career around being an expert at digital campaigning. And now you've become an entrepreneur, whether you wanted to or not. What have you learned about yourself during this transition?

Daria Grastara (18:43.534)
A lot. Yeah, I think the hardest shift was in all my past jobs, I've had to sell digital, which is so easy for me because I believe in it and I love it and it excites me. And I like getting a seat at the table in any operation I'm part of and making sure digital gets respect and budget and represented well. And now I'm not selling digital, I'm selling me doing digital, which...

Eric Wilson (18:44.59)
from expert to entrepreneur.

Daria Grastara (19:13.198)
has been very hard, like putting the me in it and getting asked on pitches, well, why you? Why direct persuasion? And coming up with that narrative and having the reasons and the results to back it up. And a challenge for me, to your last question, was usually the principles are the ones selling. And I don't.

like want to sell all day. I want to do the work, which I think a lot of people feel. And I think that's also a big barrier to entrepreneurship in this field. But I just started treating sales like a marketing campaign. And I got really, really good advice of just like, hey, you optimize campaigns all day long. You look at results, you set goals, and you work backwards, like do that with sales. And it made it a lot more fun for me and the team.

when we just treated it like, okay, we're running a lead campaign right now. And then we need to turn those leads into qualifications and then from qualifications and yes, yes. and not just rely on my network. And I think a big thing because I've been the client before so many times is I get the big wigs and to pitch me and they take me to dinner and they, you know, I earn their trust and they earn my trust and, and then they're gone and they disappear. And so,

Eric Wilson (20:14.382)
Yeah. At a very small scale. Yeah.

Eric Wilson (20:33.966)
Mm -hmm.

Daria Grastara (20:36.43)
keeping in mind because it's so fresh for me what it was like on the other side and what I didn't like. And I ran all of Trump's digital advertising in 20 and we took any pitch from any digital advertising platform. And we still at Direct Persuasion will take any pitch. I probably shouldn't say that on a public stage, but we will because we don't know what else. No, no, no. But I took every pitch and afterwards,

Eric Wilson (20:57.454)
It's Daria at.

Daria Grastara (21:06.702)
I had a few vendors say like, who's good at selling, who's not and why. And I was like, I really should write a book about selling because I've been sold to, we, we created a vendor encyclopedia internally at Direct Persuasion and we're at like 400 names of companies that have pitched us and have all their materials. And it's like, yeah, I, I don't want to be those bad salesmen. So I need to remember that because I'm not selling digital anymore. I'm selling a commodity and an asset.

Eric Wilson (21:12.622)

Eric Wilson (21:20.942)

Daria Grastara (21:35.374)
a partnership, and so switching from like the driver's seat to the passenger seat has been hard. But I also don't know if I like you become an entrepreneur. I've noticed it with my team. I think you have it in you. And I think you have the traits that make a great entrepreneur, like quick decision -making, strong gut instincts, ability to admit when you're wrong and when you need to pivot.

see farther and wider than just your day to day responsibilities and like passion and excitement. intrinsic motivation is a big one that matters so much. and just, you know, being motivated by what you want and not all the outside noise. So yeah, I don't know if I'd become one. I think it was probably my personality. Yeah.

Eric Wilson (22:15.886)
Right. Yeah.

Eric Wilson (22:28.978)
You chiseled it out of the marble. It was always there.

Daria Grastara (22:35.054)
Yeah, why I hated probably party committees because they're bureaucratic and not startup -y and why this made sense for me.

Eric Wilson (22:43.854)
Yeah, and we've talked about this before, where I'm a little frustrated at how our industry treats mid -career professionals, right? If you want to grow, you really are forced to start your own thing, go into business. There aren't many roles out there for someone who's, you know, maybe spent 10, 15 years building up skills. It's just a fact of our industry.

What's a skill that you wish you'd developed sooner before becoming CEO of Direct Persuasion or that would have set you up for, I guess, earlier success?

Daria Grastara (23:27.598)
Yeah, that's a great question. The CEO's job is to build a strong team, motivate that team, get the most out of that team. And I think how you do it is by having a purpose and a mission and camaraderie, and you're all operating off the same playbook. And I read a lot of career books and tech books and personal development books and

Product jobs are so easy to do that because you're building a tangible thing. It's been harder in the service space. And so I figured out how to hire, how to recruit, how to retain, how to keep people happy, how to keep people motivated and build a really strong operation. I think what I'm struggling with now and what I need to continue to work on is making sure that vision is very clear and understood and not assumed.

And I never needed vision in any of my jobs because I said my very first point, I always set it for myself by like having four year leaps for myself. but that's not everyone and, not everyone, you know, has a path for themselves. They want to feel part of something. And so building out that setting vision and communicating it, sometimes I just assume everyone thinks of the space the way I do on my team. And.

they know what I'm thinking and they're mind readers and they're not. And I need to be able to articulate it. So I forced myself, I like carved out, we do monthly wrap ups now where I talk about the industry and I talk about how I see ourselves in the industry or where I wanna expand to and finding areas where I have to hold myself accountable to share that with the team or doing one -on -ones and regular review schedules every six months with every single person on the team and I sit in on those.

so that they can hear where I see them fitting into the larger plan.

Eric Wilson (25:30.478)
Well, thanks Daria for a great conversation and sharing your entrepreneurial journey with us. There's a link to direct persuasion's website in our show notes. If this episode made you a little bit smarter or gave you something to think about and Daria shared a lot of really good career advice, business advice, book recommendations, you know that all we ask is that you share it with a friend or colleague.

It makes you look smarter in the process more people find out about the show. It's a win -win all around Remember to subscribe to the business of politics show wherever you get your podcasts. So you'll never miss an episode You can also sign up for email updates on our website at business of politics podcast com with that Thanks for listening. We'll see you next time

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