I started a performance-focused digital marketing agency, initially offering SEO, paid search, and conversion optimization. The early value proposition was simple: measurable growth tied directly to revenue, not impressions or vanity metrics. I began as a freelancer first, largely out of necessity. That allowed me to validate demand, refine my positioning, and generate cash flow before taking on overhead. The agency formed organically once client demand exceeded what I could deliver solo. The hardest part was turning marketing skill into a repeatable business model. Delivering results is one thing; pricing correctly, scoping work, hiring, and building systems that don't depend on the founder is much harder. My first clients came from direct relationships, referrals, and doing real work publicly—publishing content, sharing results, and being opinionated. What didn't work as expected was broad outbound and generic networking. Without sharp positioning, those channels wasted time. It stopped feeling like freelancing when clients were buying the firm, not me, and when delivery, sales, and fulfillment could run without my daily involvement. That's the real transition point. If I were starting again today, I'd niche down faster and productize sooner. Generalist agencies struggle. Clear positioning and defined offers accelerate everything—sales, hiring, and margins. Bio: Nate Nead is the CEO of Marketer.co and SEO.co, a performance-driven digital marketing firm focused on measurable growth and long-term customer acquisition strategy.
My name is Alexander and I'm the founder of Acorn Digital Consulting, a boutique digital marketing agency. I've been in the digital marketing space for close to 20 years, working with brands big and small in North America, Europe, and Asia. I also have a doctorate in a completely unrelated field (History and culture). 1. In 2024, I started a boutique digital marketing agency, focusing on offering Google Ads management, SEO, and content creation. Since then we've also branched out to focus on AI Search / AEO and more general digital marketing consulting. 2. I've worked in a freelance capacity on and off for close to 20 years doing pretty much the same things my agency initially focused on offering. I also worked at various agencies or in-house positions during that time, including long term contracts for startups and other folks. After leaving a senior management position at an agency, I started this venture as an agency founder rather than just a freelancer because I had acquire substantial business development and operational experience I hadn't had earlier in my career, and which I could leverage to aim larger. 3. The business part of it was (and is) still the hardest part of running a business. Doing the work, no problem, but managing my team, handling more finances than before, and focusing on business growth for the organization as a whole is quite different than winging it from contract to contract as a freelancer. Learning when to not work and let the team handle tasks also took some getting used to. 4. Our first clients were referrals - either from past contacts coming back or people who knew people I worked with reaching out on a recommendation. One of the first clients also came from having seen a LinkedIn post I made about starting my own agency and that kickstarted the conversation. 5. Definitely the moment I brought other people into the picture, and started paying them. Can't pretend you're a solo freelancer anymore after that. 6. Bring in at least one person to help with sales and business development side of things from day 1. It's difficult to grow a business while also focused on client relations and project tasks. Get a dedicated specialist to score leads and optimize your offers.
I started a global branding and digital marketing firm 24 years ago before Facebook or AI were on the radar. From the start we did anything a marketing department, ad agency, market research shop or PR agency did on an as needed outsourced basis. The tools and technology have changed but we continue to help our clients find the right words and pictures to create interest for their products and services. I started with a handful of former colleagues and we've grown organically over the years. My first client came from a talk I gave to a professional networking group. Someone from the audience came up to me after and made an introduction which resulted in my first project a few weeks later. It was a 1 year agreement for a 6 figure engagement which felt great that my talk was so well received and generated meetings and referrals as follow up, I knew I had a real business. I still give lots of talks and it is a great way to generate leads and business. My biggest mistake was not realizing sooner that the people you start with are not always the ones who grow with you. The hardest lesson I learned when I started my company is not getting rid of weak people earlier than I did in the first few years of my business. I spent more time managing them than finding new customers. I knew in my gut they were not up to snuff but out of loyalty to them I let them hang around much longer than they should have. It would have been better for everyone to let them go as soon as the signs were there. They became more insecure and threatened as we grew which was not productive for the team. As soon as I let them go the culture got stronger and the bar higher. "A" team people like to be surrounded by other stars. It is true that you should hire slowly and fire quickly. I did not make that mistake again later on so learned it well the first time. I wish I had known it even earlier though but lesson learned for sure! I am the founder & CEO of global communications firm Mavens & Moguls based in Cambridge, MA and my clients include Microsoft, Virgin, The New York Times Company, Colgate, venture-backed startups as well as non profit organizations. I graduated from Stanford University and Harvard Business School, serve on several Boards, am a popular speaker and columnist who has written for Entrepreneur and Forbes.
Founder - Ecommerce / 3PL / Manufacturing / Marketing at PaulShrater.com
Answered 2 months ago
Paul Shrater is a founder and operator of over a dozen companies for 20+ years, including e-commerce, 3PL fulfillment, contract packaging, foodservice distribution, and TikTok marketing. As an entrepreneur making, fulfilling, and distributing for other brands, adding in the marketing support was a natural progression. Seeing where consumers eyeballs are looking is key to understanding where to focus marketing efforts. Currently, TikTok Shop and live-selling are at the forefront. Thus, when I was approached by a Chinese agency brought to the U.S. by TikTok, I was excited to partner with them to help support integrating into U.S. consumer culture, U.S. business culture, and work to mutually bring clients into the agency. Given that China is 5 years ahead of the U.S in the world of social commerce, their consumers have built certain habits and expectations that are not yet prevalent in the U.S., thus I was able to help navigate how to take the best practices learned in China, and adapt those to incorporate how the U.S. consumer (and client brands and talent) would respond. In terms of doing things differently and lessons learned, I think there is value in working with other marketing agencies and professionals to support their clients in this specific niche of TikTok, and we are starting to do more of that now.
I started a data-driven B2B marketing agency focused on performance marketing, CRM, and analytics. At the very beginning we offered even more technical solutions, but over time we became a full-service B2B marketing agency. What is funny is that I worked as a freelancer before and in the process of funding the company. Around 3 years ago I decided to hand over the agency to someone else while I was still supporting and working with some clients. In this time I could secure a few amazing freelance/interim mandates. In these years I was able to make good money, build needed connections, and develop myself even more. Last year I became again more engaged with my "old" agency while still maintaining some smaller freelance projects. The hardest part was sales. My marketing skills were never the problem, but to get new clients, especially in the field of digital marketing, was hard. The first clients came all through my network, and it was a good base, but when we started to hire people and try to scale to a certain size, I became more and more the bottleneck and issue. In parts I was still "thinking" as a freelancer, doing too much on my own and not positioning my employees correctly. I never had the point where I thought this freelancing or an agency; it was a clear process and change. The one thing I would do differently would be to focus more on sales and building a structure there so I am not needed so much on the day-to-day client work. Also finding people that can take that kind of responsibility on their own and letting me focus on developing the company. I am Heinz Klemann, founder of BeastBI GmbH, with almost 14 years of experience in digital marketing. I love the combination of marketing and data and hope this field never gets boring.
Milos Eric is a co-founder and general manager at OysterLink, a platform for restaurant and hospitality jobs and networking. It features top-paying jobs, market insights and real-time data to help businesses and candidates stay ahead, expert guidance, and exclusive interviews with industry leaders. 1.Agency type and initial services Initially, we provided services similar to an agency but that were focused solely on hospitality through a digital recruitment, employer branding platform. The scope of our early services was to be an agency type of business that was based strictly on providing the services of Job Distribution, Employer Visibility and Candidate Matching, versus broad based Marketing Retainers. 2.Freelancer vs agency Unlike other Digital Recruiters, we did not start as Freelancers. We started the company as a Company because the business problem we are addressing requires systems, partnerships and scale. Freelancing would not have enabled us to launch successfully. 3.Hardest part of turning skills into a business The most challenging part of turning marketing knowledge and skills into a business was how to actually productize marketing knowledge and skills. Taking marketing knowledge and skills, developing a product, pricing it and creating an environment that allows companies to see the value of it are two very different challenges. 4.Finding first clients and what didn't work Most of our early clients were acquired via direct outreach or industry relationships. What we found was that trying to build the business by appealing to everyone didn't work. Narrowing the niche and gaining success with that narrow niche accelerated our ability to attract clients. 5.When it felt like a real agency We started feeling like an agency when the success of our business no longer depended on the effort of one person. When we established systems and processes that allowed us to achieve our goals without relying on a single person's involvement, we started to feel more like an agency than a freelancer. 6.What I'd do differently today If I could turn back time and start again, I would have narrowed my target market faster and said no more often. Focus is more important than flexibility in developing credibility.
Q1. We began as a full-service digital transformation agency focused on custom web development and SEO. At this point, we were largely helping small to mid-sized companies with the chasm between "you have a website" and "your website can make money". Q2. We launched directly as an agency because the vision came from a belief in collective capacity. Freelancing is about personal output, but we wanted to be able to solve complex, multi-faceted problems that required a combination of engineering, design, and marketing from the start. Q3. The hardest transition has been going from being an actor to an operator. When you are the one with the skills, it's easy to think you ought to be the one to do the work, but building a true business means you have to document the skills into processes someone else can reliably use without you. Q4. We got our first clients through direct networking and getting onto early digital marketplaces where we could showcase our depth of technical muscles. We tried broad, lead gen'ing email campaigns early that failed for lack of the specific industry context required to build connection. It seems like a reversion to form for the sector; HubSpot research notes referral and networking are far more effective for agencies than proactive cold outreach. Q5. The tipping point was realizing I wasn't on every client call and wasn't reviewing every line of thinking. It was only when my team was giving good result using the frameworks we built--without my help--that it felt like a bona fide scalable agency. Q6. If I were to do it again today, I'd narrow our focus much more quickly. In the beginning, we tried being everything to everyone, but you can only scale by owning specific real estate steeped in word of mouth. AgencyAnalytics suggests client acquisition is the top hurdle for 60% of agencies, and we find the best way to cut through that noise is specialty. I'm the Founder and CEO of Cyber Infrastructure (CIS), and for the past 20 years I've been developing digital and technological systems for scalable growth for market leading enterprises globally. I'm focused on assisting organizations with modernizing their tech stacks and deploying AI strategies for business measurable impact. Closing Thought Building an agency is a trust-building exercise at scale. It's going from "I can do this" to "we have a gather that does this", and that's a tough jump for anyone doing billable work who is looking to scale.
I am submitting on behalf of Laurel Mintz, the Founder and CEO of Elevate My Brand. 1. What type of marketing agency did you start, and what services did you offer initially? I started a full-service digital and experiential marketing agency. 2. Did you start as a freelancer first, or launch directly as an agency? Why? I launched the agency after being thrown into running another company because I knew I had the skills and drive to start an agency with my connections. 3. What was the hardest part of turning your marketing skills into a real business? I actually learned a lot of my marketing skills after starting the agency because the landscape changes so quickly. 4. How did you find your first clients — and what didn't work as expected? I found a lot of my first clients from old connections and networking. Phone and email leads were not effective for us. 5. At what point did you feel like "this is no longer freelancing, this is an agency"? Once I built a team around me that each had their unique skills, everytime became real. 6. What's one thing you'd do differently if you were starting your agency again today? I would hire an accountant much sooner. It's important to hire experts instead of torturing yourself doing work you don't know how to do. Laurel's Bio: Laurel Mintz J.D., M.B.A. is the CEO and Founder of award-winning, Los Angeles-based marketing agency Elevate My Brand serving both startups and blue chip global brands like Facebook, Verizon Digital Media Group, PAW Patrol and Zendesk.