Spin Class Case Study: So, You Want To Hang a Shingle (Part 1)
Landing your first client, building your book of business, accountabili-buddies, and how NOT to market yourself.
A few weeks ago I wrote about how I’m in my Pirate Era. It clearly struck a chord with many of you - I’ve gotten messages and comments from scores of people (some strangers, some old friends and colleagues) who are also proud Pirates, or who are now wondering if they’ve maybe been Pirates all along. This is awesome! And it also affirms a sneaking suspicion I’ve had for a while: that there are a lot of secret Pirates among us.
One of my biggest pieces of evidence? Nearly weekly for the last two years, I’ve gotten a “hey, can I pick your brain?” email, text, or DM from someone in my network who is considering striking out as a solo entrepreneur (aka “hanging a shingle”) and building a portfolio life that includes consulting/white collar service work.
I started my LLC in the summer of 2022, after 20 years in government and academia (including what I joke was my “junior year abroad” running policy comms at Twitter in 2017-2018). I quickly learned that shifting from being a high-performing leader within complex organizations to running a solo consulting business is like a wide receiver deciding to become a mountain climber. These lives use completely different sets of muscles, gear, operating environments, and definitions of success.
As I built my business and portfolio life, I solicited advice from dozens of friends and colleagues who had taken similar paths. There are SO MANY decisions you need to make when you’re hanging a shingle: your product/service offering, business structure, your price sheet, marketing and launch, etc.1 And once you start, there are so many things you just have to learn by doing: building a book of business and BD pipeline, how to balance what the market rewards with what you want to do all day, when to turn down work that isn’t right for you (for whatever reason) versus when do just do the thing. And most importantly, determining your own definition of success: in the actual work, but also in compensation, in growth and professional development, and in balancing your life outside of work.
There’s no single training, incubator, or how-to manual for solo consulting, though Katie Harbath’s work at Anchor Change comes darn close - truly, she’s been a Substack and portfolio life fairy godmother for me and so many others. One of the things Katie told me was that being a consultant can be more stable than a full-time job if you do it right. That’s definitely been my experience (though it doesn’t always feel like that every day). But getting started can feel overwhelming.
So: I thought it would be useful for Spin Class to round up some of the best advice from across our community! Today’s Part 1 will be free for everyone and cover general strategic questions about starting a solo consulting business and building out a portfolio life. Part 2 will be out next week, with more specifics on structure, pricing, tools, and other tactical advice (preview: everyone is looking for a new accountant), and will be mostly paywalled. Consider this your reminder that a Spin Class subscription is just $5/month!
HUGE thanks to Katie Harbath, Vaishnavi J., Josh Lederman, Anne Terry, Taylor Terry, Jennifer Person, Zev Karlin-Neumann, Malcom Glenn, and over 10 others who asked to remain anonymous (to be especially candid)! Their [excellent] replies have been slightly edited for space and clarity.
What do you know now that you wish you'd known when you launched?
So many folks out there are simply faking it until they make it! Not feeling like you have the exact path or understanding of how to start a consultancy shouldn’t be a barrier to taking the leap. So much of what I've learned has come from doing; in many ways, I wish I had launched even sooner than I did.
To not worry. You won't starve! But there WILL be lots of meetings about potential engagements before one becomes a client (or not). Signing a client DOES take time, even if someone seems super interested in you. It's like dating!
You actually need to practice an answer to the question, "So, what do you do?" (especially in DC). I have a few different versions of this, [including] one that centers who I work with and the problem I solve ("I work with leadership teams who can't figure out if it's a strategy problem or an execution problem or both”) and one that's legible to other people who work in the same space (“I do a mix of executive coaching, facilitation, and strategic planning").
The administrative load is going to sneak up on you. I wish I'd created a proper accounting system in the beginning. Now that I have multiple clients and expense streams, it's a bit overwhelming.
You’re almost certainly not charging enough. When in doubt, ask yourself “what would a white Republican man charge a client for this same service?”
Even friends and former clients who are excited to work with you and have project ideas for you still have to deal with realities of corporate budgets, timelines, and shifting priorities. I got very excited very early by interesting project ideas that never materialized because the client's priorities or roles changed.
The inevitable quiet periods in your business are a great time to think strategically and set up the right kind of scaffolding for your consultancy. There are many times during busy periods [when] I've kicked myself for not doing more during the quiet periods, to better support the business as a whole.
There's no one "right" way of doing things. Trust your gut, work on the things that you like, and say no thank you more.
Now that you don't have a boss, don't be afraid to take some risks. More often than not, clients appreciate your candid advice and feedback.
How do you go about building a book of business? How did you land your first client?
It's all about networking. Sharing with folks I know -- professionally and personally -- that I was starting a consultancy helped me get most of my first clients. I did come through the "front door" with a few new clients (e.g., I responded to a proposal request), but those opportunities are few and far between, and often not worth the time investment with such a low ROI.
You have to think like a salesperson and find qualified leads. If you make a list of 50 potential clients and have a connection at 25 of them, don't try to schedule 25 coffees (that will take weeks, and many of them will not turn out to be good leads). Instead, send 25 messages/emails just saying "Quick question, I'm trying to understand the market as I build my business plan; do you hire consultants for [thing you want to get paid to do]?" and follow up with "Awesome, thanks! Do you know if [other company] does?"
It took a few months to land my first client. I followed my friend's advice and talked to everyone I could - former clients, former colleagues, even people who used to work FOR me. In a lot of cases, they'd then introduce me to others. But the magic happened when I went to a small health care conference in my wheelhouse. I reconnected with former contacts, two of whom were actively seeking consultant help in areas where I am strong. I was able to convert those two projects very quickly based on that live, relationship-based interaction.
A mentor told me that most of his stuff came through peers (rather than, say, principals reaching out), and that's tended to be the case. The first one I landed solo came via a passing work acquaintance.
The people who have time to meet you for an open-ended coffee are usually not the ones who hire you.
Don't be afraid to fire a company or be fired. This business can be fluid. The day that one client told me his headquarters no longer wanted consultants (but that they really liked me and was sad to let me go) was the day another potential (and great!) client arrived in my inbox. There is not lifetime employment anymore, but there's always someone else who needs your expertise.
I've made a regular practice of catching up with and checking in on the people who know me, like me, and trust me. It almost never yields immediate returns, but has led to several cases of people coming back later because they thought of me when they had a need. I'm a generous thought partner to other solopreneurs in my network who have a hard time with proposal writing or product strategy... which often means I'm someone they call when they want to partner on things. I've joined a few benches with mixed success, and I've also been an active member of a handful of professional communities that have started to yield more opportunities to partner with people.
Product management truth: what sells the product is almost never what renews the product. So have at least one (or more) product offerings that get your foot in the door. They [should be] a thing you know organizations buy, and they're usually $5-15k.
Referrals are key. Speaking/writing/teaching/media/networking are all essential to raise brand awareness and demonstrate capabilities. My first major client knew me as a counterpart during my time in government (many years and several roles prior, and fully compliant with all legal requirements and ethics obligations).
How much do you market yourself/your business? Where? What's worked and what hasn't?
My newsletter has been the best business development thing I've done. I give them something of value, and I am in their inbox multiple times a week so if they have a project it helps them think of me. Otherwise, a lot of networking and speaking at events.
The only marketing I do is public speaking, otherwise, it's just been word-of-mouth recommendations. I don't have a website.
At present, I don't...but then I'm also not trying to do B2C. Most of the time, I'm getting hired by a VP+ member of the leadership team on behalf of their company or organization. For the most part, those people are sourcing options via their network (either asking people they trust for referrals or looking for people they already know).
I write on LinkedIn once a week. Every client I've had has mentioned how it notified them I was available, what I was doing, and they used the posts in internal conversations during the sales process.
What I've seen that doesn't work is people starting to post like crazy on LinkedIn, Substack, X, etc. when they first start out, but not being able to sustain that and then ending up with their main footprint being stale content. It's good to have searches for your name lead to something compelling, but having it be timely creates a beast you have to feed even when you're busy with other projects. If keeping a posting schedule and being interesting and topical on every post looks like what people are hiring you to do, then by all means, use that to show your chops. For most people, though, it's going to end the way every startup's blog did: the last post is going to be from years ago, dating to either right before the company found product-market fit and everybody got too busy to write posts, or about a month before they laid off half the staff to cut costs.
I have a website, but that's less about the initial pipeline and more about establishing credibility, sharing sample deliverables, and housing some ongoing projects.
I sent out an initial email blast/posted on social. Did one podcast. Have toyed with starting a regular Substack... Other than that, I haven't been especially proactive. But there will probably come a time when I'll want/need to hustle more!
Being in the mix is the key thing over fancy business cards or branding.
Speaking/writing/teaching/media/networking are all essential to raise brand awareness and demonstrate capabilities.
Being your own boss is pretty great. But what are the downsides, and how do you manage them?
It can feel challenging for the whole strategy to sit on your shoulders, especially when you're used to bouncing ideas off a team of cross-functional thought partners. I manage it by chatting more with other consultants and trying to collaborate more on projects.
Having a place on the Eastern Shore to go to on weekends to break up where I'm spending time is key. Also allows me to be outside. In-person coffees and meetings help to ensure I'm around people.
Admin, which I've had to manage by a combination of having accountabili-buddies (a friend and I literally text each other about frogs we've eaten throughout the day), routines (I now photograph every receipt as soon as I receive it), and just accepting that I only need to be "good enough" at it.
Uncertainty about the future: especially knowing the economy could implode at any minute, I'm probably taking on more work than I usually would, while it's available to build in a little cushion. But I'm also leaning into the things that being solo creates space for in my life and reminding myself that if the economy implodes, that likely would have impacted me at a full-time job too, only I'd be experiencing that without the benefits I've enjoyed from this time.
Leaning into community helps, although I have to be careful about not spending too much time with other solopreneurs when they're in the doom cycle, because the fear can be contagious.
I worried a lot about loneliness, but: I participate very actively in different communities of either former colleagues who are now solopreneurs or other people in my field. I lean into networking and have started working on a couple of boards. I have multiple work wives for one-on-one support when I need it.
The old cliche, "You eat what you kill," remains true. Staying focused and productive can be more challenging when your deadlines and targets are largely self-imposed.
Started working at a co-working space. Insist on in-persons and coffees whenever possible. I also know my product and I know marketing, but I don't know much about sales. So I started hanging out with sales consultants whose approach aligned with my values (and had good results).
Biggest downside is the part that is outside my control. When I managed my own teams in a corporate structure, I set the meetings, the structure, and the deadlines. As a client service professional, I'm now much more at the whim of the clients' needs. I enjoy the work and the clients so far - and they're all reasonable - but it's actually less control in some ways from I ran my own division.
You have to run and manage the WHOLE business, unless you are at a place where you can outsource the parts you don't enjoy (ie, accounting, marketing, invoicing, web design, etc). Look for other solopreneurs or small businesses who you might be able to barter services with. For example, if you know someone with a small startup designing websites, offer some gratis services of your own along with a killer testimonial if they consult on your website build.
When all the money is your money, it can feel hard to spend it to make a problem go away when you could handle it yourself. You have to remember that money you spend out of your business is usually deductible, so when you buy back your time by paying someone else or buying a service you're spending much cheaper dollars than the ones you use to buy back time in your personal life.
There's obviously the challenge of being one person with only so much bandwidth. I do find myself saying yes to most things, both because they sound interesting and because I can never entirely silence the voice that says maybe nothing else will come along for a while. So the risk of overextending yourself is real. I try to be organized about deadlines, and have some shorter-term projects so that I can take on other stuff when they're over. And I try to maintain a bit of slack capacity in case something exciting comes along.
It's lonely! While I get to work with the teams at client organizations, I miss the depth of work that comes from being in-house, as well as the camaraderie that comes with being part of a consistent team. The brainstorming, the constant learning, all that stuff. Be thoughtful about what you need from your work environment and how you can cultivate that as an entrepreneur.
The work will not get done unless you do the work yourself, because that's what clients are paying for. This can be challenging when multiple client deadlines converge or you have an unexpected personal/family emergency.
Those of you in politics/policy - what advice do you have for people hanging a shingle in this political climate? Has that advice evolved in recent months?
I'd generally discourage people from doing anything other than setting up a minimal LLC if they don't have ready line of sight to multiple clients. It's crowded out there, and most people who want to get back into government and policy eventually would probably be better served by spending their time on some mix of upskilling, working outside their old domain to get some breadth of experience, or even just taking a year to straighten out the rest of their lives than putting in the hustle and sunk costs it will take to build a business only to walk away from it once the tide comes back in. Some of this is a question of what you can afford, whether you can move away from DC and easily come back, and what your network is up to. But I'd only start down this path if you want to be a consultant in the long term.
As a former civil servant, I've always presented a non-partisan face to the world, so can call politicals in this administration as much as I could during the last. I do modify my talking points to reflect this administration's priorities, but that's just good messaging.
It's definitely a dicier moment, but I've honestly been pleasantly surprised that clients still want/need support even when Kash Patel could be breaking down their doors any moment.
Pitch yourself as a solution to the problem of living through the Trump era. For example: if you're a university cutting costs because funding has dried up, I can understand why you might not want to splurge on crisis comms. But, isn't telling a better story the best way to protect/advance your agenda?
Lay a long-term foundation. There may be some easy money to be made [by working with certain clients], but it may come at the expense of future opportunities, income, or reputation.
I'm not in politics or policy, but have many DC friends and am sending you all the most love and righteous rage.
Looking back, what's the single most useful piece of advice you got on hanging a shingle?
Focus on the BD channels that are the most energizing and fun for you. You won't see me on LinkedIn because I loathe every second I spend there. But you will see me sending you a text or email to catch up.
Ensure you have multiple income streams, so if one ends you have others to lean on while you find others.
So much of the guidance out there is SPECIALIZE! FIND YOUR NICHE! But that can lead you to over-invest in niches that either aren't a good fit for you or don't have a viable total addressable market/price point - and then you risk completely missing directions that could be better for you. So many solopreneurs try to make fetch happen out of the gate with a niche that is based more on their dreams and passions than a viable market. Try not to specialize in the first year or two. Take a wider variety of projects and pay close attention to what energizes you, what tends to go well, etc.
Get really clear on both your revenue number, your time horizon for getting it, and your reasons for going solo in the first place, and let those things drive your pricing and BD strategy. Otherwise, for most of us, the default pattern is to maximize revenue, which risks recreating many of the toxic patterns that we were trying to escape by going solo in the first place.
From the podcast Design Yourself: "The way it feels along the way is indicative of how it's going to feel when you get there." If you got into this because you wanted to slow down your life, but are chasing BD and marketing at 150mph, my prediction is you're going to wind up recreating the exact same dynamic that led you down this path in the first place.
Prioritize finding an "anchor client" - one that reliably and consistently brings in enough business to keep you going and gives you the flexibility to pursue smaller, less lucrative projects that are often the most meaningful.
Go talk to people before you're ready, before you've finished building the thing you want to build.
Stay open to a wide range of possibilities - don't narrow your focus too quickly. This year, I'm doing a mix of freelance writing, product marketing strategy, and innovation workshops - potentially with some leadership coaching on retainer. They're all related to my focus on helping people have more meaningful conversations to stimulate growth, but how I help those clients can take many different forms.
Don't undervalue the things that come easily to you. Those are your superpowers and your real value to clients. Just because you do it effortlessly and joyfully, doesn't mean you should charge less for it.
Get a bank account as soon as you have your government documents in order, and do it at the bank where you have your personal accounts so that money transfers are same-day.
“Never go head to head with Emily Horne."2 For real though... maybe just the colleagues who have encouraged me not to sell myself short? After being a staffer for years, being at a principal's beck and call, it can be hard to remember that a) you have something of value to offer, which you don't have to give away for free; and b) that it's OK to set boundaries about you charge, what hours you'll work, etc.
Don't try to hang a shingle and interview for full-time work at the same time. It's a recipe for failure. And trust your instincts: better to walk away from a potential engagement than be mired in a bad engagement.
Less a piece of advice, and more a comment a friend made to me when I tentatively shared an idea with her. She said: "Your success is inevitable." That has carried me on tough days.
Part 2 next week, including:
Structure (LLC, S Corp, etc.)
Finances (accounting, retirement, etc.)
Pricing (everyone’s biggest questions and where people are by FAR the cagiest in getting specific— but we will!)
Coming up with a name was a unexpectedly tricky for me! It took me forever to come up with Allegro (which I love). I swear, every corner of every Washington, DC neighborhood has been used in an LLC name.
I swear he actually wrote this and I did not pay him to do so!