How to make a living while you’re making a difference. A weekly show for independent professionals who want to go from six-figures to seven while increasing their impact on the world.
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Eliminating Friction
When outsourcing is freeing vs. when it simply adds more friction to your life.How to tell the difference between good friction and bad friction (hint: it’s not the same for everyone).Why it makes perfect sense to outsource critical functions that are not core to your business—think taxes, legal, payroll.The surprising benefits from documenting what you do and how you do it.The human side of heavy outsourcing—and how to decide if it’s for you. Quotables“I don't really care about search. I care about word of mouth. So if people aren't searching for my name, I'm doing something wrong.”—JS“After that first week (without my VA) I literally wanted to gouge my eyes out.”—RM“When it's literally done, it's different than knowing it's going to get done.”—JS“I'd like to not do it (the outsourced task), but I love the feeling that it's done and I don't have to worry anymore.”—RM“It would be silly to do your own books or legal…things that are just not core to your business.”—JS“I want to outsource the things that bring me comfort or bring me to a different level.”—RM“I can't stress enough how important it is to have the steps of any of your processes written down.”—JS“Having that checklist means not having to dedicate a space of your brain to anything routine.”—RM
Setting Your Own Agenda
The questions to ask yourself if you want to start or stop providing a particular service to a particular client.Breaking up with your client: when to do it, how to do it and what to watch out for.Why you always want to build a time constraint when transitioning clients—and how to think about the transition process.When retainer scope creep is your fault—think guilt around doing less for a bigger retainer—and what to do about it.Why the consultant’s job is to hold the vision for the project (and who is always THE client).Quotables“Here's the thing, it's your business. If you want to stop doing tactical work, you do more strategic work.”—JS“Breakups don't have to be ugly, but the other thing is that sometimes what we think might lead to a breakup doesn't at all.”—RM“Once you start doing that (extra pair of hands work), then it's a slippery slope. All of a sudden it's like the architect is cleaning the bathrooms.”—JS“The client asks because they don't think about our business model. They assume if they ask us for something that doesn't make sense, we'll say no .”—RM“The perfect time to say no…is the first time, like when the first ask happens or when you first think you're going to do it of your own volition. The second best time to do it is right now.”—JS“It's really important to be clear about your timeline so that your clients understand that there's a limited timeframe and if they don't move, they're not going to get support.”—RM“But if you have one foot out the door, it totally changes the framing (of your message). And then they're like, wait, maybe there's something we can work out.”—JS“Holding the vision for the project, that's our job. And if I want to get dramatic, I would say it's a sacred obligation.”—RM
Are You Feeling Lucky?
How to move beyond magical thinking and get very specific about your dream clients and buyers.Why crystal clear positioning makes everything—including attracting your ideal clients—flow more easily.Improving your odds of successful matchmaking—allowing influential others to hook you up with “your people”. The relationship between taking calculated risks and achieving oversized outcomes (think drumming with the Foo Fighters).Matching your dream up to your business and revenue model—and why that’s so critical.Quotables“If you could just wave a magic wand and be working with your top 20 dream clients, what names would be on that list?”—JS“In most situations, success is hard work plus opportunity or as someone famously said, ‘The harder I work, the luckier I get.’”—RM“You can increase your luck surface area, meaning you can do things, you can do the work, put in the effort to make it much more likely that you're going to attract the right kind of opportunities.”—JS“We want to be a thoughtful matchmaker—it’s what we hope to receive from the people matchmaking us.”—RM“Books will have this tendency to give you a defacto positioning.”—JS“When we first start businesses, we're not always that clear about where we’re going—it’s like binoculars that you keep focusing.”—RM “There's this outbound thing where you can take control of fate and say, okay, that's my dream. Tesla marketing. That's all I care about. And you put all of your resources into that for a period of time.”—JS“We want to see you succeed when you are the underdog…I want to see you strap on the cape and fly off into the air.”—RM
Making Your Email Newsletters Relatable with John Dick
How the newsletter started and why it was a well-kept secret for years.Tying the newsletter to the core business without making it salesy or deadly dull—and positioning it differently than anyone else in the space.How he sets the flow of the newsletter—and his fear that eventually he’ll run out of stories (sound familiar?).His #1 rule before releasing any “What We’re Seeing” emails.Why typical business assumptions about corporate titans are wrong—and how to engage them.Quotables“I wanted it to be the kind of thing they would want to read while drinking their coffee in the morning or laying next to their spouse in bed, on their phone. That's the vibe I was going for.”—JD“I was quite apprehensive initially about even doing something weekly. Cause I was like I once you're on the ride, it’s hard to get off.”—JD“It's gotten harder because I've used up most of my good stories by now, like funny stories I have from my dad or my college or whatever and like all my best material, I worry sometimes that I've used it up.”—JD“An insight is significantly more valuable the more relatable you can make it.”—JD“When you can make the insight…it doesn't just allow us to connect with that person as a reader, but it allows them to actually use that insight to drive a decision that they have to make.”—JD“I do think there are the people who read that and they see I'm not exactly sure what this company does, but I want to do business with people like this.”—JD“My Saturday email gets to be a little bit of a sacred place where that (sales) stuff doesn't happen.”—JD“I can tell you without ever naming any names, the most senior people and powerful people on that list are the ones who are most likely to answer those frivolous poll questions at the end of the newsletter.”—JDLinksCivic Science Twitter
Zero To One
What it takes to put your first product out for the world to see (even if you’re not painting zombies on skateboards).The fears you may experience the first time you go public and how to push through them.Why publishing your price(s) attracts the right buyers and repels the bad-fits.Worried about leaving money on the table by quoting a flat price? How to think about that whole transaction differently.Why your prices for products and productized services are all experimental and deserve to change regularly.Quotables“I was aware of a sales guy who would routinely send out proposals with an extra zero. And if the client gasps, he's ‘oh, it's a typo. Okay. Sorry. Sorry. It's $60,000, not $600,000.’”—JS“The buyer's time is valuable too. Who's going to want to sit through three conversations with three unknowns to figure out what they're going to do?”—RM“Just put a price on your website and you'll automatically attract the right kind of people for you. It would save everyone time. You wouldn't have to negotiate.”—JS“That first time that you actually put a price on your website…all sorts of things come up in your head, including imposter syndrome.”—RM“There's this fear of leaving money on the table, but guess what? If somebody jumps at it, then you just raise the price for the next person.”—JS“If you don't ever try raising your prices, you won't know the upper limits of what you can charge.”—RM“That indifference to whether or not the client buys—generally that comes from being in demand.”—JS“There's just something about putting a price on your website—you’re making a statement, oh, this is not a cheap WordPress guy I can hire for a thousand dollars…That’s level setting.”—RMLinksCarl Richards on Ditching HourlyAsk us a question
Monetizing Your Positioning
How most freelancers and independent consultants monetize their expertise in their first year or two—and the signs when your revenue model might need an overhaul.The link between your positioning and monetizing your business—and why you want to be open to new ways of packaging your expertise.A “typical” consulting/speaking/book revenue model and how it can become a trap (and some ideas to avoid it altogether or get out while you can).What to do when your revenue model isn’t working.Quotables“It's very common for people to just go out on their own and do their job, but for clients instead of a boss, and the obvious business model is to just rent your hands out by the hour. And that's fine. That'll get you going.”—JS“And then at some point (after you’ve positioned yourself) you come smack dab up to your business and revenue model and you say, oh, these don't fit anymore.”—RM“The competition is increasing and you start to realize that you need to, you might not call it positioning, but you start to realize that you need to appear different in a meaningful way.”—JS“The real money is coming from the other two revenue streams (consulting and speaking), so he is on what I would call a gilded hamster wheel.”—RM“The typical business model for a consultant is write books, speak at conferences and make your money on consulting…He couldn't sell that business—he is the business.”—JS“This idea that you're stuck with this business and revenue model that you created for something you no longer do is insanity.”—RM“I love posting prices on your website because it puts you into a slot in the prospect's mind. So when new clients come along, they already have the expectation, at least in a ballpark way, of what it would mean to work together.”—JS“Of course, there are things you're going to do for free. But when you're working in your genius zone, delivering to your ideal audience, most of those should be paid.”—RMLINKSInequity aversion
Patterns Of Authority
You’re spending considerable time thinking, writing, speaking, publishing and socializing your point of view.You discover the forms of publishing that fit with your talents and audience and produce regularly, no matter what.You’re building a niche that not only allows you to charge more for your specialty, but gives you the ideal audience to continually feed your curiosity and work from your genius zone.You’re positioning your business and expertise in white space—a target market that you don’t share with anyone else.You’re building a business model with seductive levels of flexibility: what and how you charge; how much and how often you work; and a suite of leveraged services and products that optimize how you spend your time.Quotables“If you are renting your hands out by the hour to do tasks for your clients, it can be difficult to carve out time (to build authority). That feels un-billable, it feels like you're losing money.”—JS“Authorities have a point of view: what is your belief system about how your expertise impacts your world?”—RM“Freelancers are basically selling their hands where authorities are selling their brains. It's all about the intellectual property."—JS“Obviously you can make a lot of money specializing, but in addition to that, you really can go where your curiosity takes you.”—RM“Since I've got a daily deadline to publish something…for a bunch of people who are waiting for it, my brain will gravitate to what I should consider for that vs. thinking about say what should I wear tomorrow.”—JS“If you're looking for ways to prime the (authority building) pump…read!”—RM“Writing is like the sort of cohesive, coherent long form. It’s the crucible almost that you go through to bake your idea into something.”—JS“A lot of us need to socialize things with other people to really get at all the things in the dusty corners of our brains.”—RM
Do You Need An Exit Plan?
Situations where designing an actual exit plan makes sense and how to think about it.The mindset required to move from trading time for money to creating assets with value independent of your presence.Client exit strategies and why they worked for their situations.Creating a business where the value isn’t 100% tied to your name—and when/how to start the shift.
The Post-COVID Reckoning
Channeling that sense of dissatisfaction to make big, small and/or pivotal change in your business.Deciding which aspects of your work/life are ready for change and how to keep moving forward.Dealing with status and identity challenges as you evaluate what next steps will work best for you.Leaning into small changes that can have an outsized impact on your happiness.How to let those clients and employees you’re leaving behind go with integrity.Quotables“I like to think optimistically that the whole thing was a wake-up call for people—who are now feeling the malaise as a desire to have more of a purpose or impact.”—JS“Our elbows are rubbing up against the sides of our cage. And people are saying, what else is there? What can be next?”—RM“Everything's in motion. So any rut that you're stuck in, you're going to have a lot of helpful momentum to pop you out of it.”—JS“Don't worry about the process. Worry about where it is you want to go to get really excited about your work again.”—RM“If you could wave a magic wand and put whatever you wanted in your calendar, what would be in your calendar?”—JS“Change begets change. We do one small thing and then it energizes us, it gives us confidence to make another change.”—RM“Look at your product and service mix and ask: am I getting bored with these? Am I getting better at these? Are they aligned with my mission?”—JS“We like the changes that we initiate far more than those that somebody else puts on us.”—RM
Avoiding An Expiration Date
Evergreen expertise and content vs. those with an expiration date.How to distinguish yourself with evergreen content—and why your voice and point of view are clear difference makers.Avoiding the purist view that we absolutely have to invent something that's never been thought of before—and what to do instead.Side-stepping the eventual conversion of your hot market knowledge into a commodity—or worse (our sympathy to Flash developers).The magic of moving up to a higher level topic that is relevant to your current audience—and how to do it.Quotables“Maybe you localize a topic about marketing or sales into the technology landscape that didn't exist five years ago. If you’re careful about how you straddle that divide, you could still create very evergreen, but up to date content that stands the test of time.”—JS“It's really easy to say let's go do evergreen content, but to distinguish yourself, you've got to really slice and dice it in such a way that you've got something new to say, or it’s new to a different audience.”—RM“I've probably read 200 books on sales and marketing. It's stuff that software developers would rather eat glass than read. So if I can bring that to them in a funny way, or a way that resonates with them, or using language that doesn't repel them, then that's super valuable.”—JS“We can't come from this purist view that we absolutely have to get something that's never been thought of before.”—RM“Some of these more evergreen topics are going to be like fundamental truths of human nature, human behavior.”—JS“It's a lot easier to get attention when you've got the newest sexiest whistle—everybody wants to go hear it.”—RM “When you’re being cutting edge, you're co-opting the hype that some product or technology has built up and you're just strapped to that horse.—JS“When your consulting is based on a new technology, over time more people are going to know what you know, so the price of your expertise goes down and eventually becomes commoditized.”—RM
Addicted To Being Busy
Tackling the mindset that says you must be constantly busy or you’re not worthy of success.Busyness as a form of procrastination—and what to do instead.Why defining a clear goal and strategy (with pre-planned tactics) can help you side step unfocused busyness.The joys of creating leverage—and what to do with the time you’ve freed up.How intentional, goal-based action will naturally identify the most high impact moves to grow your business.Quotables“When you actually get productive instead of just busy, you're producing better output with less input.”—JS“There is busyness that is not productive in some way or creative, but that is really designed to take up space—it keeps you from facing decisions you need to make.”—RM“Strategy is what helps you understand the difference between an opportunity and a distraction.”—JS“Not checking or responding to email constantly really changed my life.”—RM“How do you get productive instead of busy?”—JS“Putting some limits on what you do in a day helps to improve productivity and outcomes.”—RM“If you find that you can't eliminate the busyness, you have to ask yourself: what's going on here? Am I hooked on it? Is it some kind of worldview? Is it my identity? Do I believe deep down that if I'm not toiling all at all times, then I'm a bad person?” —JS“If you recognize that maybe there's a little addiction going on with your busyness, before you start to shift gears, just stop and breathe for a moment and just ask: is this the best thing for me to be doing next?”—RM
Engineering Confidence
How confidence plays out in growing your business—and the role of daring and initiative in your success.Why you need a handful of marketing processes built around your expertise and your market position—and a few examples of those that work. How to think about and design your selling systems with both fixed and fluid components. Ensuring your delivery processes support your selling and marketing and deliver your promised outcomes.Why your behind-the-scenes operations need processes too—including project management, invoicing and client/team communications.Quotables“It's not confidence that allows me to launch (something new). It's that if it doesn't work, I'll try something else.”—JS“Well-placed confidence says, listen, I've been through this before. I don't know if it's going to be successful, but I'm confident that I'm going to do my best to make this work.”—RM“What is the market telling me…is this thing I created not selling at this price? What am I learning from that? And how do you build a system around it?”—JS“It's hysterical how those checklists save us time, but they engineer confidence. Because you can focus on what's important vs. the miscellaneous stuff that has to get done.”—RM“If you have to learn the lesson every time…you're not engineering any confidence in your process.”—JS“When it comes to selling, you want to absolutely systematize every possible thing.”—RM“You’ve already burned the creative energy to come up with a really good way to say this—why reinvent the wheel?”—JS“Process is absolutely a critical part of being a believable, repeatable, successful consultant.”—RM
Battling Invisible Risk
Understanding how bad things could go—what’s the worst that could happen and how are you protected?Pricing your work based on the amount of risk you decide to shoulder.Saying no to high risk, low return client requests.The role and value of defining work processes to manage your risk exposure.Using peers and sounding boards when you’re doing strategic, high-impact consulting.Quotables“What's the right thing to do when you're engaged in client projects, where there are risks and project failure can cost lots of money?”—JS“How bad can things go and what's your role in that? That's a strategic business operational question that we all have to ask ourselves.”—RM“If you…take these hidden risks and make them visible, you can price based on that.”—JS“Most of us who go into our own businesses, we don't like the word discipline…but there's a certain amount of discipline in running a business.”—RM“E+O insurance, that was my net. Like I could walk the high wire with confidence, knowing that if things went as bad as possible, I wouldn't be in the street. My family wouldn't be in this.”—JS“If what you're doing is more of a strategic thing, you really want to have a sounding board or two that you can use when you uncover an unusual client situation.”—RM“Knowing that a second pair of eyes will be reviewing your work is a very interesting little kind of safety valve.”—JS“We had peers excited about the work that we were doing, trying to figure out how to make it great for the client.”—RM
Everything You Want To Know About Retainers
How to structure—and think about—advisory retainers, including the role/importance of a guarantee.Operating as a fractional CXO without committing to hours.Designing extra pair of hands retainers that focus on outcomes—including productized services sold monthly.The landmines to avoid when structuring your retainers.The mindset shifts you’ll need to make as you move along the retainer continuumQuotables“In this context you're selling insurance…that's what an advisory retainer is. It's not about showing up and coding.”—JS“When you're used to being paid for using your hands, being paid to sit on them instead feels really weird.”—RM“The people who designed my Subaru Outback are different from the people who built my Subaru Outback and are different from the people who change the oil.”—JS“You're not going to be able to deliver a home run to somebody who can't figure out what that looks like.”—RM“If you're earlier in your career…and you do want some kind of stability or predictability in your income you could sell productized services on an ongoing monthly basis.”—JS“There's no shame in doing the work and creating some kind of a retainer where you can get stability, you can get some continuity and you can build your credentials in the course of working for those organizations.”—RM“What are you guaranteeing with an advisory retainer? The thing that I would guarantee is the response time. What they're buying is good answers fast.”—JS“The whole idea behind advisory retainers is they're buying access—to your brain and to good answers fast.”—RM
Ask Us Anything 4
The role of trust—in you, in the process and their ability to carry out your recommendations—in choosing their course of action.How differing perceptions of risk and the fear of change can drive organizational decisions.Getting behind surface reactions and digging more deeply into the “why” behind client decisions.The relationship between time, value and urgency as the client perceives them. How the perhaps invisible—but still deeply entrenched—internal politics of your client’s situation may play out.Quotables“Straight up fear of change—where there's a perceived risk—it feels scary. Or distasteful. People just don't like change.”—JS“Forget what you think is the right decision—just try to get to the bottom of what the client’s fear is about. By asking them some of those deeper questions, you may be able to uncover something that isn't on the surface.”—RM“Sometimes it’s that they do trust you and they're not afraid of change, but they recognize that it (your recommendation) could fail.”—JS“If the person who's making the decision doesn't reap any of the benefits, they're just not interested in putting their head on the chopping block.”—RM“Maybe the person who's making the decision is new and hasn't got the political capital to do it.”—JS“The whole theme of this is don't rely on your logic. Because your logic doesn't matter. It's how the client looks at it—it’s their perception of the situation that is going to drive the decision.”—RM“Money is only part of the investment. There's also a time investment for any project.”—JS“This is not about being manipulative. It's just really digging in to their situation and trying to understand what their life is like inside this organization.”—RMGot a question for us?Do you have a question that you'd like us to answer on the show? We'd love to hear from you! Email a voice recording to Jonathan at asktboa@jonathanstark.com and we'll add it to the queue.