ļ»æDave de Cespedes Full Interview Transcript
Thriving Through Podcast - Episode 72
Air Date: January 8, 2026
THE PATH TO SELF-EMPLOYED CONSULTING
AJ: Welcome to this episode of the Thriving Through Podcast. Today, my guest is Dave de Cespedes. Dave, welcome to the podcast.
Dave: Very excited to be here, AJ.
AJ: Well, let's dive right in. What was your path to becoming a self-employed consultant?
Dave: I'd say it was a pretty winding path. I started my career in architecture and got into operations work, started an agency with my brother, a creative agency, got into education, and have been doing my consulting now for the past four years.
I think I just got into it, sort of fell into it, I guess. I think I was creating content around productivity and productivity methods for teams, and what works and what doesn't. And that just snowballed little by little into working with clients and ended up building a business around it.
THE DEFINING MOMENT: TESTING THE WATERS
AJ: Okay. Was there a particular defining moment when you said, absolutely, this is what I want to do?
Dave: Yes, so I was... this was back in I think 2021. I was teaching, working with high school students, and I had started getting some leads for one-hour calls and strategy sessions for usually entrepreneurs and very small teams, and it was January, it was the start of the year.
I was at a bit of a crossroads. My wife was pregnant with our second daughter at the time. And I decided, let's see if there's enough demand for this work. So for that roughly five months, I was essentially working two full-time jobs, was teaching during the day, and working with clients on odd hours and weekends, early mornings.
And I got to the summer where I had four active clients that were retainer-based, so I had enough traction to dive in and say, I set a goal, and it looks like there's enough demand, and just kind of jumped in from there.
AJ: Okay. You didn't go back to teaching in the fall.
Dave: That's right, that's right.
BIGGEST CHALLENGE: MANAGING SEASONAL FLUCTUATIONS
AJ: Okay, so tell us a story about the biggest challenges you faced building your practice and how you overcame them.
Dave: I think one that comes to mind that I maybe wasn't entirely prepared for was the ups and downs in leads coming in. And for everybody who's consulting, you probably know that as we get closer to the end of the year, things quiet down a bit, and then we get into January, February, and everybody wants to get started yesterday.
There's, you know, and we get to the summer, and there's some quieter periods there. So definitely in my first year, that was something to get acclimated to, to really make sure that I had enough of a roadmap to say and prepare in advance to say, what does my capacity look like, and make sure that I'm not overworking myself at any given time.
And also, I'm accounting for those down periods and having a strategy in place, maybe reconnecting with previous leads, or reconnecting with contacts that, for one reason or another, didn't turn into projects. And just kind of having a game plan for how to account for that, just to make sure that I didn't end up running out of gas, or running out of runway, and staying ahead of that as much as possible.
AJ: That makes a lot of sense.
BIGGEST LEARNING: STAYING CURRENT WITH CLIENT NEEDS
AJ: So you've been at this four years, self-employed. What has been your biggest learning since you began your consulting business?
Dave: That's a big one. I think one that is top of mind now is the importance of staying up-to-date as much as possible with technology, with tools, with clients' pain points. I think some pain points are pretty universal across industries and across teams.
But a lot of them shift just based on the times, and I think now a big focus as the majority of my clients are starting to think more intentionally about adopting AI, and what does that mean for workflows, what does that mean for team collaboration.
Making sure that I'm carving out enough time to stay up to date with what those pain points are. That means reconnecting with previous clients, keeping up relationships, just being proactive about asking those questions to previous clients or non-clients, just people in my network.
And making sure that, you know, on the tool side, I'm also keeping up with what's available to teams, and I think when it comes to AI, new models are released, what seems like every month, and with new capabilities every time there's a new release.
So making sure that it could be hard to carve out time for your own research and your own professional development, but I think it's definitely a key to staying ahead, and to make sure that you do continue to provide value, and you can solve the problems that clients are having, and the problems that they have top of mind.
AJ: I really like what you said about going back to talk to previous clients and maybe even prospects, so you can double-check and make sure that the pain points have not changed. Or what new pain points have come in with the tumultuous world we live in, especially with AI.
And, you know, I face this, one of the challenges, we could spend all of our day just learning new AI tools, so that we can recommend them to our clients. So it's really, it's all happening so fast that it can feel a little overwhelming. But it sounds like you devote some time to it.
THE SOLO CONSULTANT CHALLENGE
Dave: Yeah, 100%, and you know, as a solo consultant, I chat about this with clients all the time, that not being on a team, you're kind of wearing all of the hats, right? You're your own business development team. You're, you know, working on proposals, selling, strategizing, and then also delivering on the work. And all of those different departments that would usually exist in a bigger company, now it's all just you, right?
And so making sure that you do carve out time for, you know, what you're not seeing in billable hours, but the non-billable work that does directly impact your work and your ability to add value to clients. So, you know, it can be easy to just kind of put that on the back burner and say, I'm billing at this rate. I'm going to do this work and just do that for a set number of hours. But I do think that's a recipe for, you know, going a bit stale and getting a bit dated and feeling a bit out of touch with what's happening.
And I think that is incredibly important, and there is an element of just being proactive about how you're doing that. And I think to your point about the AI tools and even tools outside of the AI space, there's just so many products and so many tools released almost on a daily basis.
And I think one thing that has helped me is leaning heavily on, like, peers and other consultants and communities that exist for independent consultants to kind of share what they're learning about and what might be interesting to kind of dig into. And so there's that kind of collective intelligence side of things that's been incredibly helpful.
And then also just being okay with not being an expert in everything, right? I'm focused right now on Notion and AI, and helping clients integrate those types of tools and kind of set up their workflows. And, you know, there's obviously a very wide spectrum of tools that teams are using or can use, and I'm okay with not being an expert in every single one of those.
And, you know, sometimes clients will ask about my expertise or my familiarity with a tool, and I can just be honest about that and say, look, I can do some research, and I can kind of get up to speed, and that's going to be a learning curve. But I will get up to speed on it, or I can just point you in the direction of someone who is more familiar with that tool and bring them into the conversation as well.
AJ: I think the willingness to say, I don't know everything about everything, and I can connect you with the right expert for the things I'm not an expert in, is a really important part of being a trusted consultant.
Dave: Absolutely.
BUILDING RECURRING REVENUE THROUGH RETAINERS
AJ: So when you first started and you had the four clients on retainer, is that something that has continued throughout your business, having retainer clients? And if so, can you tell us a little bit about the importance of recurring revenue?
Dave: Yeah, absolutely. It's definitely continued. I'd say those retainer clients are the backbone of the business. There are usually one-off projects or strategy sessions or quick calls that come in here and there, but those retainer clients, and ideally growing that over time, is really where the stability comes from.
And, you know, to your point on just the recurring revenue side, you know, I think the biggest advantage is that, you know, when you get to the 1st of the month or when you're kind of doing your financial planning, you know what you have coming in, and you can plan around that.
And so whether it's, you know, investing in the business, whether it's, you know, taking a training or taking a course or investing in, you know, a tool or some professional development or hiring, you know, to offload some of the work, you can kind of make those decisions because you have a foundation of recurring revenue coming in.
AJ: That is excellent advice and good things to aspire to.
TRANSITIONING FROM HOURLY TO VALUE-BASED PRICING
AJ: So did you start your business by hourly billing, or did you start with retainers and project-based work?
Dave: I started hourly and very quickly shifted away from that. I think within the first month or so of working with clients, I realized that it is a bit of a race to the bottom when you're pricing based on hours.
And I think there's a few reasons for that. I think, number one, you're incentivized to take longer on projects, right? If you're billing by the hour, the more hours you put in, the more revenue you generate. But on the flip side, that doesn't really reward efficiency, right?
So if you're able to solve a problem in half the time because you've done it before or because you've developed a system or a template, you're essentially penalized for being efficient. And I think that's not really aligned with the value that you're providing to clients.
And I think on the client side, they're, you know, they're focused on the deliverable and the outcome, not really on how long it takes you to do that work. And so I think shifting to value-based pricing or retainers or project-based work, it kind of shifts the conversation from, you know, how many hours are you going to put in, to what's the outcome? What's the value that we're creating? What's the ROI on this?
And I think that's a much healthier conversation to have with clients.
AJ: I agree with you 100%. And I think one of the hardest things for consultants to do is figure out how to price themselves when they move to value-based work. So can you share with us how you think about pricing for value-based work?
Dave: Yeah, absolutely. I think it's a combination of a few different things. I think, number one, it's understanding the scope of the work and what the deliverable is. And I think being as clear as possible on that front helps you understand, okay, what's the time investment going to be? What are the resources that I'm going to need to bring into this?
But I think beyond that, it's also understanding what the ROI is for the client. And that's a conversation that I think sometimes consultants shy away from because it feels a bit salesy or it feels a bit pushy. But I think it's actually incredibly important to understand what success looks like for the client.
And if you can tie what you're doing to a measurable outcome, whether that's time saved, whether that's revenue generated, whether that's, you know, cost savings, or just efficiency gains, I think that helps you understand what the value is that you're providing.
And so, you know, for example, if I'm helping a team implement a system or a workflow that's going to save them five hours a week, and you know what the hourly rate is of those team members, you can do the math and say, okay, over the course of a year, this is what this is worth to the organization.
And I think when you frame it that way, it becomes a lot easier to say, okay, here's the investment, and here's what you're getting in return. And I think that's a much more compelling conversation than just saying, this is going to take me 20 hours, and I charge this much per hour.
THE IMPORTANCE OF SYSTEMS AND ORGANIZATION
AJ: One of the things that I find interesting is that many consultants struggle with systems and staying organized. Can you talk a bit about how you stay organized and the systems you use to run your practice?
Dave: Yeah, absolutely. I think it's critical. And I think, you know, again, wearing all of the hats as a solo consultant, if you don't have systems in place, you're going to feel incredibly overwhelmed and kind of drowning in all of the things that you need to keep track of.
I think there's a few different systems that I think are critical. I think, number one, just having a CRM or a way to track leads and clients and projects. For me, I use Notion for that, but there's obviously a lot of different tools out there that work really well.
But I think just having a single source of truth where you can see, okay, here are the active clients, here are the leads that are in the pipeline, here's where they are in the sales cycle, here's the last time I followed up with them. Having that visibility is incredibly important.
I think also on the project management side, you know, making sure that you have a system for tracking deliverables and deadlines and milestones. And I think that's true whether you're working with one client or ten clients. You need to have a way to say, okay, here's what I need to deliver this week, here's what's coming up next week, here's what I need to be thinking about in the next month.
And then I think also on the operational side, having templates and systems for things like proposals and contracts and onboarding and offboarding clients. I think the more you can systematize that and the more you can kind of templatize those processes, the less time you're spending on that administrative work and the more time you can spend on the actual revenue-generating activities.
And I think also just reducing that cognitive load of having to reinvent the wheel every time you bring on a new client or every time you send out a proposal. I think that's incredibly valuable.
AJ: That's really smart. And I think especially as a solo consultant, you don't have the luxury of having an operations team or an admin team to handle all of that stuff. So the more you can systematize it and make it repeatable, the more time you free up to actually do the work and serve your clients.
BUILDING COMMUNITY AND AVOIDING ISOLATION
AJ: You mentioned earlier about the importance of community and connecting with other consultants. Can you talk more about that and how you've built community around you?
Dave: Yeah, absolutely. I think it's critical, especially as a solo consultant, because it can get very isolating. And I think, you know, when you're working from home or you're working remotely, and you don't have colleagues to bounce ideas off of or to kind of vent to when things are frustrating or to celebrate wins with, I think it can feel very lonely.
And so I think being intentional about building community and finding peer groups has been incredibly important for me. And I think there's a few different ways to do that. I think, number one, there's online communities and forums and Slack groups and Discord servers that exist for independent consultants and freelancers and solo entrepreneurs.
And I think finding ones that are active and where people are generous with their time and their advice and their experiences has been incredibly valuable. And I think, you know, being able to ask a question and get feedback from five or ten people who are in similar situations or who have been there before is incredibly helpful.
I think also on the more formal side, you know, there are coaching programs and mastermind groups and accelerators that exist for consultants. And I think those can be really valuable because they provide structure and accountability and, you know, a regular cadence of check-ins and conversations.
And then I think also just, you know, reaching out to other consultants in your network and saying, hey, do you want to grab coffee or do you want to hop on a call and just chat about what's going on in our businesses? I think those informal conversations can be incredibly valuable as well.
And I think, you know, the combination of all of those things has been really helpful for me to feel less isolated and to have people to kind of learn from and to share experiences with.
AJ: I think that's really important. And I think a lot of consultants, especially when they're first starting out, feel like they need to have all the answers and they need to figure everything out on their own. And I think the reality is that building a network and building community and being able to learn from others who are a few steps ahead of you or who are in similar situations is incredibly valuable.
SETTING BOUNDARIES AND MANAGING CAPACITY
AJ: One of the things that I think is a challenge for a lot of consultants is managing capacity and setting boundaries. Can you talk about how you think about that and how you manage your time and your energy?
Dave: Yeah, absolutely. I think it's critical, and I think it's something that I'm constantly working on and trying to get better at. I think the challenge with consulting is that, you know, there's this pressure to always be available and to always be responsive and to always be working.
And I think especially when you're first starting out and you're worried about where the next client is going to come from, it's very easy to say yes to everything and to overcommit and to take on more than you can handle.
And I think, you know, what I've learned over the past few years is that that's not sustainable. And I think, you know, if you're working 60, 70, 80 hours a week and you're constantly stressed and you're not sleeping and you're not taking care of yourself, that's going to catch up with you.
And so I think being intentional about setting boundaries and managing capacity is critical. And I think there's a few different ways to do that. I think, number one, just being honest with clients about your availability and your capacity.
And I think, you know, if a client comes to you and says, hey, can you take this on? And you know that you don't have the bandwidth, I think it's okay to say, look, I'd love to work with you, but I'm at capacity right now. Can we schedule this for next month? Or can we bring in someone else to help with this?
I think also just being intentional about your schedule and blocking off time for, you know, non-billable work and professional development and rest and recovery. I think it's very easy to just pack your calendar with client calls and client work and not leave any time for yourself.
And I think, you know, making sure that you're building in buffer time and making sure that you're taking breaks and making sure that you're taking care of yourself is incredibly important.
ADVICE FOR CONSULTANTS JUST STARTING OUT
AJ: So as we start to wrap up, what advice would you give to someone who's thinking about becoming a self-employed consultant or who's in their first year of consulting?
Dave: I think the biggest piece of advice I would give is to test the waters before you jump in. And I think, you know, for me, that meant working two jobs for five months and building up a foundation of retainer clients before I made the leap.
And I think that's not possible for everyone, and I think there are situations where you need to make the leap before you're 100% ready. But I think if you can, validate that there's demand for what you're offering before you quit your day job or before you go all in.
And I think the other piece of advice I would give is to focus on building recurring revenue as early as possible. And I think, you know, one-off projects are great, but they're not predictable. And I think if you can build a foundation of retainer clients or recurring revenue, that's going to give you the stability to weather the ups and downs and to invest in your business and to sleep better at night.
And then I think the third piece of advice is to build community and to find peers and to not try to do it all on your own. I think consulting can be lonely, and I think having people to learn from and to share experiences with and to hold you accountable is incredibly valuable.
FUTURE VISION: BEYOND TOOL-SPECIFIC CONSULTING
AJ: So you mentioned earlier that you're focused on Notion and AI right now. Where do you see your practice in three to five years? Is it still Notion, or are you expanding into other tools?
Dave: I'd say it's getting harder to predict with any kind of certainty with how fast tools are changing, and with AI specifically. But yeah, I think ultimately I enjoy working with teams to figure out how do we decide what decisions to make that are going to make our lives easier, and hopefully be able to make better decisions and move faster.
And I think every client I work with, it feels like every team member is wearing multiple hats and is bouncing around between ten different tasks, and it's just very hard for teams to pause and to zoom out and say, okay, how can we be doing this better? What tools or solutions are available that we maybe didn't know about? And how do we at least explore whether or not this is a good fit for our team?
It's very hard to do internally, and I think when clients reach out, or when they're interested in working together, I think it's because, ultimately, they just want someone else to say definitively, this is what we're doing, this is how it's going to work, and these are the milestones that we need to make sure everybody on the team hits.
Almost getting into coaching mode, or trainer. And then executing. So, you know, I think, at least in the foreseeable future, I feel like that's always going to be a need to have someone come in and just solve a very specific set of problems to enable teams to do their work better.
So, in terms of the tools or the details on how that's going to work, I have less and less of an idea every day that goes by, but hopefully I'll figure it out.
AJ: Well, and you're doing your homework. You're keeping up.
Dave: Yep, yep, as much as I can.
RAPID-FIRE WRAP-UP QUESTIONS
AJ: Well, as we come to the end of the podcast, I always end with a, I call them the rapid-fire wrap-up questions, and I have two questions. What's one book, podcast, or other resource that has been invaluable to your consulting practice?
Dave: I'd say lately, Traction, just covering the EOS framework. It's a book that I read probably a few years ago now, and just recently revisited, and there's so many useful takeaways in there. I think the target audience is CEOs of larger organizations, but there's still so many useful takeaways for solo consultants and independent consultants. I think just kind of reframing it.
And in terms of podcasts, I'd probably have to go with 20VC for a few reasons. Number one, it's my sort of edutainment podcast, where, on the one hand, I'm learning more about the venture space. You know, it's largely interview-based, and there's so many useful nuggets to just get a sense of what that day-to-day looks like from the inside of a VC firm.
And I think just a general curiosity in investing. I think if I were to fast forward 10 or 15 years, having the ability to angel invest or to be more directly involved in investing, I think is a big goal, and that one, I rarely miss an episode when that one comes out.
AJ: Okay, 20VC. And here is the single most important question. How can listeners connect with you if they want to learn more about you and your work?
Dave: Yes, so on my website, which is workcraft.co, that is my kind of landing page for all things consulting, and also on socials, usually using at NotionCoach. That's on LinkedIn, X, Instagram. Pretty active on all of the above, and probably most active on YouTube, which also has the same handle, at Notion Coach. And yeah, anywhere and everywhere, happy to connect with listeners.
CLOSING
AJ: Wonderful. Well, thank you. Thank you so much for being my guest today. A lot of good nuggets coming out of this podcast. So, thank you very much. And for all of you listening, until next time, keep thriving through.
Dave: It was a pleasure. Thank you, AJ.
