Never Stop Selling: A Blueprint for Coaching Success
Never Stop Selling: A Blueprint for Coaching Success
Building a thriving coaching business requires more than just great coaching skills. It demands consistency, relationships, and a commitment to always keep selling. These are the lessons Jason Pond, a CEO, serial entrepreneur, and business coach with over 30 years of experience, shared in his recent appearance on The Amanda Kaufman Show.
Jason’s journey from running traditional businesses to coaching service-based entrepreneurs offers a wealth of insights for coaches at any stage of their careers. Here’s a closer look at the strategies and principles he discussed to help you grow your coaching business.
1. Never Stop Selling
One of the most critical pieces of advice Jason emphasized is simple but powerful: Never stop selling.
“Many coaches make the mistake of landing a few clients and then completely shifting their focus to serving them,” Jason explained. “That’s a recipe for an empty pipeline.”
Jason stressed the importance of maintaining consistent outreach and lead generation, even when you’re fully booked. By keeping your pipeline full, you’ll avoid the feast-and-famine cycle that plagues so many entrepreneurs.
Amanda echoed this wisdom, sharing her own experience of overcommitting early in her coaching career. “I learned the hard way that building capacity and keeping sales consistent are key to sustainable growth,” she said.
2. Build and Nurture Relationships
Coaching is fundamentally a relationship business. Whether it’s with clients, collaborators, or referral partners, Jason believes in the power of fostering authentic connections.
“Relationships are everything,” Jason said. “I spend time engaging with potential clients and partners through outreach, attending trade shows, and staying active on platforms like LinkedIn and Instagram.”
He shared how he uses his podcast to connect with other professionals who support small businesses. “It’s a great way to learn from others, build a referral network, and stay top of mind for future opportunities,” he added.
Amanda underscored this point by highlighting the importance of diversifying your networks. “I even keep a pipeline of potential suppliers,” she said. “Relationships open doors you never even knew existed.”
3. Embrace Accountability
For Jason, accountability is a non-negotiable part of success. He credits his involvement in coaching programs as a source of motivation and structure for his own business.
“I joined a coaching program because I needed that weekly push,” Jason said. “The accountability of being asked, ‘Are you doing your reach-outs? Are you keeping your pipeline full?’ keeps me on track.”
Amanda agreed, sharing how her own accountability practices include daily non-negotiables and regular check-ins with her coaching group. “Accountability transforms intentions into action,” she said. “It’s why coaches exist—to guide and hold their clients to their goals.”
4. Understand Your Capacity
One of the most common challenges coaches face is managing their capacity. Jason shared his own experience of overcommitting to a single high-ticket client early in his coaching journey.
“When that client moved on, I realized I didn’t have a pipeline to fall back on,” he said. “Now, I’m more strategic about balancing my capacity and ensuring I always have opportunities in the wings.”
Amanda emphasized the importance of planning capacity in advance. “Taking a deposit and scheduling a start date a few months out is a simple way to manage your workload without sacrificing quality,” she explained.
5. Don’t Rely on One-Off Efforts
Jason dispelled the myth that a single marketing effort—like launching a website or posting an ad—will flood your calendar with clients.
“In two and a half years, I’ve yet to get a client from a single website post,” he admitted. “Success comes from consistent, ongoing outreach and follow-up.”
Amanda agreed, highlighting how staying visible and top-of-mind is essential. “The reality is, people won’t engage with you unless you make it easy and consistent,” she said. “One email or one post isn’t enough—you need to show up repeatedly.”
6. Be Willing to Push and Receive Feedback
Jason also shared what he believes makes a coach truly impactful:
Listening more than talking.
Providing direct, honest feedback.
Pushing clients in ways their friends and family wouldn’t.
“Coaching is about helping clients see what they already know but aren’t ready to admit,” Jason said. “It’s not always easy, but it’s necessary to create real transformation.”
Amanda reflected on her own journey to becoming a better coach. “It took me years to learn how to push clients effectively, but it’s one of the most rewarding parts of the job,” she said.
Final Thoughts
Jason Pond’s story is a powerful reminder that running a successful coaching business requires both strategy and heart. By staying consistent in sales, nurturing relationships, and embracing accountability, coaches can build a business that not only thrives but also transforms lives.
If you’re a coach looking to take your business to the next level, start by asking yourself:
Am I consistently selling, even when I’m fully booked?
Am I building and nurturing relationships across multiple networks?
Do I have the accountability I need to stay on track?
By focusing on these areas, you’ll set yourself up for sustainable success in the long run.
Connect with Jason and Amanda
Want to learn more from Jason Pond? Connect with him here:
Stay tuned for more episodes and resources from Amanda Kaufman:
What’s your biggest takeaway from Jason’s advice? Share your thoughts in the comments or send this article to a coach or entrepreneur who needs to hear it!
Chapters
00:00 Introduction to Jason Pond and His Journey
03:55 The Importance of Continuous Selling
07:37 Building a Sustainable Coaching Business
11:19 The Role of Relationships in Coaching
13:20 Lead Generation Strategies for Coaches
19:31 Surprises in the Coaching Industry
21:49 Key Elements for Coaches to Succeed
Full Transcript
Jason Pond (00:00)
I came in thinking I knew everything about how to run this type of business that I had sold to them. And as I started to realize, I started to research that, no, I didn't know anything.
I knew how to run my business in my very, very tiny 1500 person niche of a client base, but it was not anything to where I, what was out there in the world. And that's when I started to read Patrick Lanchoni's books. I read the E-Myth by Michael Gerber. I read Good to Great and Built to Last by Jim Collins and all of the great business books that through there. And that's when I started to realize that, wait,
Amanda Kaufman (00:17)
Right.
Jason Pond (00:42)
There's other ways to do things. And it became very interesting. It's like, how do you make a great company from the get-go, kind of like in Built to Last, but then keep it going beyond what he even talks about in some of his other books.
Amanda Kaufman (01:18)
Well, hello and welcome back to the Amanda Kaufman show and we are continuing our series on the coaches that don't suck. I am so excited to have you here today, Jason.
Jason Pond (01:30)
Thank you, Amanda. Appreciate being on the show.
Amanda Kaufman (01:33)
Love it. Well, dear listener, with over 30 years as a CEO, serial entrepreneur and business coach, Jason Pond has scaled and sold multiple businesses, experiencing firsthand the challenges and rewards of entrepreneurship. Now he helps driven clients turn challenges into big wins using the same principles that have guided Jason's own successful exits. So, Jason, I'm so excited to have you here on the podcast.
I'm so curious, what, maybe just take 30 seconds and update us on like what are you working on now and who are you focused on helping?
Jason Pond (02:12)
Yeah, man, a great question. I am focused on helping the small business service based business a lot in the broadband industry to help grow past the ceilings that are holding them back and kind of break through with the same spots where I was. I would love to be able to help them pop their egos, just like I was able to get my ego popped back in 2016 and started to figure out coaching.
and joining a coaching program in 2018 and going forward. So I do holistic business-based coaching. I focus on five pillars that I created around the system of your four standard pillars of business and then adding in that self-development piece. And we do it in a community-based setting where we're every week and we're continuing conversations and it is just having a fantastic way to...
facilitate these service-based businesses and give them a spot to ask questions just like they would at like a trade show or a conference where they're going to learn information about what's going on. They get to do it every single week.
Amanda Kaufman (03:21)
love that. That's so great. And, you know.
the momentum that you've got with your business right now, I think is gonna be very inspiring to a lot of our listeners because we have a lot of listeners who are just starting out with their coaching business. They've got kind of their first few clients and I'm always really excited to have a fellow business owner who has some significant business experience to just kind of like shine a light on some of the things that maybe we could be doing differently as coaches. This is the coaches that don't suck segment. So I am really
curious like you mentioned 2016 was the time that your ego got popped. Tell us more about that. What do you mean by that?
Jason Pond (04:04)
Yeah, so what happened was I was a I was that technician. If you've ever read the E myth, the and I had sold my business. Yeah, so I had sold my business at that time and I went to work for a company that was a little bit of a train wreck. And there they had there was a lot of projects off track. There was a lot of cooks.
Amanda Kaufman (04:11)
my God, I love that book.
Hmm.
Jason Pond (04:27)
and there's a lot of cooks in the kitchen per se, if we're use some analogies today. And I came in thinking I knew everything about how to run this type of business that I had sold to them. And as I started to realize, I started to research that, no, I didn't know anything.
I knew how to run my business in my very, very tiny 1500 person niche of a client base, but it was not anything to where I, what was out there in the world. And that's when I started to read Patrick Lanchoni's books. I read the E-Myth by Michael Gerber. I read Good to Great and Built to Last by Jim Collins and all of the great business books that through there. And that's when I started to realize that, wait,
Amanda Kaufman (04:49)
Right.
Jason Pond (05:14)
There's other ways to do things. And it became very interesting. It's like, how do you make a great company from the get-go, kind of like in Built to Last, but then keep it going beyond what he even talks about in some of his other books.
Amanda Kaufman (05:30)
love this and I'm a big reader as well. If you were to chat with say somebody who's starting their very first online business, they wanna coach other people, you mentioned that there were like five pillars that you teach from. What would you say is like the top wisdom that you would share now that you've spent so much time with so many different businesses? What do you think a coach should make sure they're doing?
Jason Pond (05:56)
I made the biggest mistake that a lot of coaches make, and that is you get a couple of really good big clients in and you stop selling. Don't stop selling like never stop. Yeah, never stop selling. And if and if it means you have to grind it out, like a lot of times we see coaches jump into this because they want to get out of the corporate grind, right? They go from corporate into into coaching and.
Amanda Kaufman (06:06)
Woo!
Never stop selling.
Mm-hmm.
Jason Pond (06:24)
I've watched those guys and they they'll jump in. They'll get a few clients and then they'll back way off. Right. They stop selling inside of it. So that's definitely the biggest element to it is don't stop selling. Keep that pipeline full, even if you have to delay bringing onboarding a new client like that's that was something that I didn't realize. I got to start serving them tomorrow if they sign up. No, they can agree to sign up and you can start serving them in two months and build the built.
Amanda Kaufman (06:31)
Mm-hmm. Mm-hmm.
1000
% yeah and like mechanically when I'm doing that is I just take a deposit You know and we get the agreement done. So then it's like, okay There's some commitment here and then you know, we we can pick up a little bit later I love this like
Jason Pond (06:53)
capacity into it.
Amanda Kaufman (07:10)
So I myself came from corporate. I myself had that exact same experience. I got about 18 months into the game and I had 16 private clients. I'm meeting with them for full day intensives. I'm meeting with them every single week. And I just found myself time poor. And I found my cash flow got way out of whack because I kept investing and getting more help and more support in retrospect.
very prematurely. So if anybody has not read
Profit First by Mike McHallowitz. Anytime the subject comes up, I'm pretty much recommending that book. But the E-Myth is a really good one too. I think one of the biggest transitions that I had to make to enable me to sell all the time and keep that process going and keep that process sustainable for the level of capacity that I actually had for both time and money, it required me to kind of take the coach hat, just...
turn it down a little bit and turn up the I'm a CEO, I'm a founder, I'm an entrepreneur hat and like really embody that. And it fundamentally changed a lot of the decisions I was making. I'm really curious, like what do you do to keep your pipeline full? How do you keep that spark alive for pipelining?
Jason Pond (08:28)
It's challenging, when the because I've been in that spot, I've been in that spot of it was completely dry. I had a very big coaching client and the we were working, you know, six figure ticket, you know, private coaching client. And it was a I'd put all my effort into them.
didn't have a pipeline. All of a sudden it was like, well, we're we're done here. We don't need to continue this conversation. I'd coached him up to a point where I couldn't help him anymore. And then I moved on. It was time to move on. And then I looked out and I went, no, I've got I have lots of good runway. But when I'm looking at that runway, I'm going, it's getting it's getting tight. And remembering that is what keeps me going on.
Amanda Kaufman (09:07)
no, I know.
Jason Pond (09:21)
doing reach outs, you know, and, you know, joining a program. So myself, just as I've met you, I joined a coaching program so that I was being coached also. Right. And I'm getting pushed and driven every week. Similar style program, but I'm getting pushed every week. Like, are you doing the opens? Are you reaching out and getting those pipelines going? And that helps keep motivated because there's accountability.
Amanda Kaufman (09:31)
Exactly. Yeah.
Jason Pond (09:49)
If you don't have an accountability partner, chances are you're not gonna do it. Because we're, humans, we are designed to conserve energy.
Amanda Kaufman (09:59)
percent.
Yes, but at the same time, we're also like biologically wired for social connection and maintaining our status in the tribe, right? So, you know, I still have like behind me, behind the computer here, my five daily non-negotiables. And I've got an accountability meeting later today with members of that coaching program. And it's like, if I show up to that call and I'm not posting to social media, you know, three times a day and I'm not doing five.
And I'm not taking 45 minutes for my movement and my body and myself. And I'm not reading. I feel like a schmuck. I think that a lot of times, and I'd love your coachy perspective on this, a lot of times people allow pain to become the brakes.
Right? So the pain, you you strike me as a bit of a techie whiz or, you know, like a technical expert. And I'm kind of the same way. I'm super happy reading. I love doing my journaling. like, I'm probably one of those people that if there was kind of an apocalypse situation and I had to like live in a cave for a year, I'd be good. You know, like I would be okay. But coaching is a social game, right? And I'm always telling my clients like coaching is ultimately a relationship. So even if you
Personally really enjoy that solitude or you identify as an introvert
The choice to coach means you're making a choice to be good at relationships. So, you know, the way I've done it is I've looked at it as a skill like anything else. And I've worked on skill all the way from, you know, meeting strangers to, you know, sparking conversations and relationship with those strangers to nurturing those those relationships forward and so on so that I always have a consistent pipeline of collaborators, a consistent pipeline of clients, a consistent pipeline, you know,
of
affiliates, it's, in my business anyway, I've got like five different pipelines. I even have a pipeline for potential suppliers that might come in and do you have any idea how many people have pitched to fix my YouTube channel, right? So my first move that I do with them is I invite them to fill out a form to be a preferred supplier. So then when I need to tap that pipeline, I'm gonna go to the people that take the time to do a form as like the first opportunity to do that work.
Jason Pond (12:22)
love that. I'm implementing that like this week. So that's fantastic.
Amanda Kaufman (12:27)
Do it, do it, right? Yeah, you know why I did it is because I hated doing DM outreach because I knew that I was gonna get pitch slapped with things that I wasn't ready to buy. And it was getting in the way of me building authentic relationships. So was like, you know what, if I can have an authentic response to that.
invitation, then I can gracefully dismount the conversation and I can again, you know, pick the conversation up when I'm good and ready to. So yeah, it really helped with my outreach.
Jason Pond (12:54)
Yeah.
That sounds great. Absolutely on that side.
Amanda Kaufman (13:01)
Yeah, I love it. So Jason, like, how do you go about doing your lead generation and everything? You know, I think a lot of coaches, I've actually just recently ran a survey for our audience and the I would say the number one thing that came back was this desire to attract.
people who were interested in buying coaching. And I think what's really wonderful about having you here on the show is your audience isn't other coaches necessarily. It's small business owners. So how do you go about like building the initial, like the early pipeline with the marketing to generate the leads that you can then reach out to?
Jason Pond (13:39)
So I've gone a couple of different ways. And one of the ways is that is working really well is as I created a cold email outreach that went out and solicited people to be on my podcast. And that generated it was just a matter of what I was looking for was referral partners on the through that. And it's kind of morphed a little bit to.
Amanda Kaufman (13:55)
interesting.
Jason Pond (14:05)
I love having the conversation with them. I'm getting to learn a lot about different businesses that support small businesses, such as digital marketing agencies, other coaches and various different, you know, I do holistic business coaching, but I've talked to sales coaches and marketing coaches and, you know, other life coaches, mindset coaches, various different people that support small businesses. And so I've used that to help gain into a referral network.
I'm also doing a lot on LinkedIn and getting a lot of engagement and reach out on there. I've added Instagram here in the last couple of months. So I'm starting to do some more reach outs on that side of things. Yeah, thanks to that one. And I've done a lot of direct and I'm actually attending the industry trade shows also and having conversations.
Amanda Kaufman (14:42)
Yeah, hard not to in that coaching program.
Jason Pond (14:55)
I come from the industry though. So I've, I was in this industry for 20 years before I decided to start coaching in the industry. And it's, and so I've, have a lot of vendor relationships. I have a lot of other relationships with other providers that were inside of the industry. And I was able to go and sit and have conversations with them and just continue to foster relationships. Right. And that's all it is, is just continuing to foster a relationship until the point.
Amanda Kaufman (15:04)
Mm-hmm.
Jason Pond (15:24)
of which they have that click in the mind, like, I wonder, would this work for me, which can open the sales conversation for us to have, then eventually close a deal and get them into the community.
Amanda Kaufman (15:36)
I really appreciate that very detailed answer because I think a lot of people kind of have this expectation when they're starting. I know I certainly did that when I get the certification, I'll hang my shingle and then every like my calendar is going to be completely flooded. I was actually really nervous about that. But the hilarious thing is at the time I had eight people in my immediate network that I felt comfortable saying like, hey, so I'm starting a new thing. Maybe like you might want to try it.
And I was so shy and so bashful, but I think that beginner overwhelm is just thinking that you are going to launch the website and all of a sudden you're going to go viral and there's going to be this huge onslaught.
Jason Pond (16:18)
this total.
Total fear of success, right? I mean, that was like I would I hesitated and hesitated and hesitated as I wrapped up a contract with my previous company that I sold. I was like, I can't launch yet. I'm going to get inundated. I don't I got to be able to serve the customer. I to be able to serve the customer and or the client and the coaching case. And yeah, that same thing like when got the certification.
Amanda Kaufman (16:25)
Totally.
Holy.
Jason Pond (16:47)
put it up there, decided to post it in one spot and thought that, this is going to get lots of views. have yet in two and a half years, I have yet to actually get a client from that one posting that came up. Everything else has been through other outreach.
Amanda Kaufman (17:01)
Yeah,
exactly. I think the big kind of bubble that we're popping here is just bursting the bubble of just taking out an ad is enough, or taking out the website is enough, or sending one email is enough. It's like, no, no, no.
What does it take for other people to get into relationship with you? Like really look at that, you know? So I was talking about the onslaught of people doing outreach to optimize my YouTube channel, which by the way is very slowly and surely working because we have done a lot of optimizations on that YouTube. I'm probably going to hire some time soon, but and that's actually a really good point is like.
I've been getting outreach by dozens of these people that are offering to do this optimization. And so what is it naturally doing? It's naturally causing my brain to go, maybe I should do that.
Maybe that is something I might consider doing. And there's that top of mindness. Now, a lot of those vendors are not going to get my business because I never see them again. They don't have a social presence. They're not reminding me that they're there. You know, they're not reaching out again after I say my initial no. Right. And by the way, if you're watching this and you're this far into the episode, mention the episode and then I'll know for sure that you're serious about making a relationship here. And like I think I think a lot of coaches don't realize just how much they push the
world out and away and require so much of others to have relationship with them and then they're super surprised when it's the same same out in the world.
Jason Pond (18:37)
Yeah, that's great, great, great perspective.
Amanda Kaufman (18:39)
Yeah, yeah.
Yeah, totally. And I think what I also really appreciated about your answer is that, you you used your past relationships like I'm coach that didn't, but like you're probably...
Like I don't know the size of your business, but you're probably much further along than I was at two and a half years because I was requiring that I start from the tiny list and I was requiring that I do all networking to build my relationships. I had all these constraints and requirements and I wasn't tapping into that past network and I wasn't, know, so it was all starting from scratch. So it's like, like if we just assumed our businesses were roughly the same size at this point.
You can get to the size you wanna get to even if you don't have a big network you can reach out to, but just expect that that's gonna take a lot more time, right? And if you give yourself permission to access the network, that's pretty huge. Okay, what was one thing that surprised you when you pivoted from traditional business and into coaching specifically?
Jason Pond (19:31)
Yeah.
Ooh, that is a really great question. The one thing that surprises me the most, and it surprises me and frustrates me, and I haven't figured out the best way, but that is I thought a lot more people would be interested in coaching. And it's like, I got interested in coaching, and so I thought because I was interested in coaching, everybody else was gonna be interested in coaching.
Amanda Kaufman (19:53)
Mm.
Yeah.
Jason Pond (20:10)
And the surprising thing is, that a lot of society today cannot look past the end of their nose. It a little bit of a call it.
Amanda Kaufman (20:19)
Yeah, I think there's a lot of suspicion
in people volunteering to help and it's like, what's that gonna cost me? And there's also like lot of this fierce independence. No, I can do it myself, right?
Jason Pond (20:32)
Yeah, I can do it myself. I don't need to help that technician mentality. of like, if I have to do it better than anybody, I'm the only one that can do it better than anybody else. Right. So it's, you know, to be able to crack the code of.
and get into the people that are willing to start to look outside for help and realize that by looking outside for help, they actually propel their businesses sometimes 10X faster than if they're just sitting down and grinding them.
Amanda Kaufman (21:06)
.
for sure been my experience is one of the reasons that I love supporting coaches because I know that the actual product of coaching, especially when done well, can be such an amplifier and it can also increase the quality of what you do and it can reduce so much cost as well, right? Because if you kind of think about stumbling around in the woods without a map, right, versus working with a coach, you know, even if the coach is not prescribing the map per se, they're just helping you slow down and make higher quality decisions according to your values to
Something as relatively simple as that can cost you so much less in the long run because you're not, again, stumbling around in the dark and not evaluating your options properly. So that's so cool. All right, I'd love to ask this question on this segment. Jason, what do you think are three things that help a coach not to suck?
Jason Pond (21:49)
Yeah.
Three things that help a coach not to suck. Inside of coaching, when you're in the program, three things are, they are listening more than they're talking.
Amanda Kaufman (22:01)
Yes.
So good.
Jason Pond (22:09)
So
the objective is just to be able to learn from your clients and find those spots where there is the nuances to help guide the conversation. Because really we're guiding them to the answer that they already have. They just don't, they're not willing to admit they know it, right? So there's one. Two would be, it's.
Amanda Kaufman (22:25)
Exactly.
Totally.
Jason Pond (22:35)
very hard to give a direct feedback. And people don't like to get direct feedback, but a coach that doesn't give direct feedback is not doing you justice. It's and it can be very painful inside of it. And I would say three that they're willing to go out of their way to support you and push you in ways that your friends and family
Amanda Kaufman (22:48)
So true. Yeah, absolutely. That took me a few years.
Mm-hmm.
Jason Pond (23:04)
or others would never do. They're willing to say, like, they're willing to really say, like, and tell you the hard, the hard things that just aren't a matter of it, of what, you know, especially your friends might tell you at a Friday night party, which you shouldn't be at if you're trying to run a business, by the way, you should be trying to run your business and not partying. But it's your friends might tell you, but your family would never tell you.
Amanda Kaufman (23:07)
I love
Mm-hmm.
Mm-hmm.
Jason Pond (23:33)
that you need to not be doing 35 things. You need to focus on one part of your business.
Amanda Kaufman (23:40)
Yeah, yeah, exactly. I'm a certified high performance coach, and that's with the High Performance Institute, led by Brendon Burchard. And I think the poor man had to say, they pay you to push only about 30 times before I was like, right, right, OK. And I had to find my way of pushing that was congruent, because ultimately it is a relationship.
You know, I think that that's a very important for any coach to do rather than just be another body, another warm body in the person's network. So good. So Jason, if people wanted to keep up with what you're up to or follow you, what's the best way to do that?
Jason Pond (24:18)
Yeah.
Best way to do it is on Instagram. It's at Mountain Freedom Coach. And if they want to DM me AK for Amanda Kaufman, I will get them a free one hour coaching session.
Amanda Kaufman (24:41)
outstanding. That's amazing. I mean, y'all, 30 years of business experience. This dude knows what he's talking about. I would definitely take him up on that. And, dear listener.
Don't forget to subscribe. You know, if you've loved this episode, make sure you smash that subscribe button on wherever you're listening to. you know what, if you just take a few minutes to do a review, leave us five stars. Jason worked really hard on this episode. Leave us five stars so that other coaches are gonna find this episode and be, you know, find the utility out of it. And in fact,
You probably know three people who would really benefit from this conversation. If they're you know, stutter stepping and not getting started with their sales or they had some initial success, but they're not keeping their consistency. Who are three people you know that would really benefit from this short conversation about how to stay connected with your coaching business? Thank you so much for joining us, Jason.
Jason Pond (25:42)
Thank you, Amanda. It has been such a pleasure to have a great conversation.
Amanda Kaufman (25:46)
Amazing. Thank you, listener, and we'll see you on the next episode.
