Unlocking Success as a Solopreneur: Insights from Shelly Oswald

Building a successful business isn’t about having it all figured out from day one. Contrary to the common myth that entrepreneurs “pop out of the womb” ready to run a company, seasoned business coaches like Shelly Oswald know firsthand that business success relies on learning key skills and developing strong support systems.

Shelly joined The Amanda Kaufman Show to discuss what she calls "the business side of business" and to share practical strategies for solopreneurs feeling overwhelmed and stuck.

The Business of Doing Business

With over 35 years of experience across brick-and-mortar and online ventures, Shelly focuses on the often-overlooked foundational elements of running a business. These include managing finances, selecting the right tech tools, and creating systems for repeatable success.

Many solopreneurs are skilled in marketing or product creation, but they often struggle with the financial and operational side of their business. Shelly’s role is to bridge that gap.

“If you’re a solopreneur struggling with systems, overwhelmed by bookkeeping, or just unsure how to organize your workflow, you’re not alone,” Shelly explains. “A lot of people think that if they’re good at what they do, they’ll naturally know how to run a business—but that’s a skill set that takes time to develop.”

Facing Overwhelm and Avoiding the “Hustle Trap”

Shelly and Amanda dive into the challenges of burnout and hustle culture.

Shelly emphasizes that working smarter, not harder, is essential for long-term success. In many cases, clients come to her only after they’ve hit a breaking point—whether from a lack of systems or feeling overwhelmed by daily tasks.

Shelly advises, “Being proactive about business skills is crucial. Don’t wait until you’re drowning to get organized. Invest time early in setting up basic financial practices and creating a rhythm to your work.”

Why Systems Matter—And Why They’re Often Ignored

One of the most common misconceptions among new entrepreneurs is that they’ll establish systems “later, once things take off.” However, Shelly points out that waiting for success before getting organized can lead to burnout and missed opportunities.

From setting up QuickBooks for managing finances to maintaining a consistent calendar, Shelly’s coaching emphasizes practical, implementable steps for building structure before chaos takes over.

Amanda shares similar observations, noting that some solopreneurs normalize overwhelm as a part of success, which can become an unhealthy habit. “A lot of marketing training encourages a ‘one-hit wonder’ mentality,” Amanda says. “But effective marketing—and effective business—is about establishing a consistent, rhythmic system.”

Empowering Clients, Not Doing It for Them

Shelly’s journey from consulting to coaching is rooted in her desire to empower her clients to take charge of their business operations.

Rather than managing their tasks for them, she teaches solopreneurs to own their processes. “I realized I wasn’t doing anyone a favor by taking on their work—I was disempowering them. As a coach, I want to help clients build the skills they need to sustain success on their own,” Shelly shares.

What Makes a Great Coach?

Toward the end of the conversation, Shelly outlines the three qualities she believes are essential for a coach who truly makes an impact:

1. Asking the Hard Questions – It’s crucial to push clients to reflect deeply and honestly.

2. Balancing Empathy with Accountability – Coaches need to provide support while keeping clients responsible for their progress.

3. Staying Organized – A great coach models the organization and consistency they want to instill in clients.

Amanda adds that while it’s easy to start a coaching business, true success in this field requires dedication, discipline, and the same kind of systematic thinking Shelly advocates for solopreneurs. “The coaching industry has a low barrier to entry but a high barrier to success.

To thrive, you need systems that support meaningful client relationships and sustainable growth.”

Wrapping Up: Tools for Transformation

One of the projects Shelly is most excited about is the upcoming launch of her custom-branded Kajabi app, which will make her community and courses more accessible to clients on the go. This app promises to streamline learning and keep clients engaged in a central, easy-to-access platform.

For solopreneurs looking to move from overwhelmed to organized, Shelly’s insights are invaluable. Whether you’re at the beginning of your journey or looking to elevate your current business practices, embracing the “business side of business” can lead to greater stability, efficiency, and success.

Connect with Shelly

🌐Website: ShellyOswald.com

📸 Instagram: https://www.instagram.com/iamshellyoswald/ 

Shelly previously certified as a Profit First Professional and Pumpkin Plan Strategist and is not actively providing those services, however, you may go here to find a pro that is active if you need help with Profit First.

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Episode Chapters:

0:00 - Introduction to Shelly Oswald
Amanda welcomes Shelly, CHPC coach and seasoned business consultant, and introduces her background in helping solopreneurs build effective business systems.

1:35 - What “The Business Side of Business” Means
Shelly explains the importance of learning and managing the financial, operational, and tech aspects of running a business.

2:30 - Why Financial Literacy Matters for Entrepreneurs
Shelly highlights why financial skills are essential and shares her game-changing experience with the Profit First method by Mike Michalowicz.

3:58 - Shelly’s Entrepreneurial Roots
Raised in a family of entrepreneurs, Shelly shares the lessons she learned from watching generations of family business owners overcome challenges.

5:10 - The “Hustle Trap” and Why Working Smarter Is Key
Shelly discusses the pitfalls of hustle culture and the importance of focusing on sustainable, proactive planning rather than reacting to daily crises.

6:25 - Facing Overwhelm: Why Systems Are Essential
Shelly and Amanda talk about the value of creating systems and how solopreneurs can start building structure to avoid burnout.

8:20 - From Consultant to Coach: Shifting to Empower Clients
Shelly reveals why she transitioned from consulting to coaching, empowering clients to take charge of their own business systems.

10:00 - Why Solopreneurs Avoid Systems and Organization
Amanda and Shelly dive into the reasons why entrepreneurs tend to delay setting up systems, and how to break free from the cycle of “I’ll organize once I’m successful.”

12:02 - What Makes a Great Coach?
Shelly shares the three essential qualities of a great coach: asking tough questions, balancing empathy with accountability, and staying organized.

14:05 - Building Rhythm and Consistency for Sustainable Success
Shelly explains why consistent systems—not quick fixes—are key to lasting success in both marketing and operations.

15:20 - The Kajabi App: Shelly’s Latest Project for Client Support
Shelly talks about her custom-branded Kajabi app, which will help clients stay connected with her community and courses on the go.

16:45 - Closing Thoughts and Takeaways
Amanda and Shelly wrap up with final insights on what it takes to build a fulfilling, sustainable business, and how solopreneurs can avoid burnout by investing in solid systems.

Full Transcript

Interview with Shelly Oswald

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[00:00:00] people think you pop out of the womb with, understanding business and that it's some sort of big failure if you don't get it.

[00:00:07] It's a skill just like everything else that needs support.

[00:00:10] So true. I'm excited to find out that you are a profit first pro that book if you haven't read profit first by Mike Michalowicz, just stop whatever you're reading, read that first and go back to whatever you were reading before.

[00:00:24] That method literally saved my business a few years ago

[00:00:28] [00:00:30] Mhm.

[00:00:47] well, hello, and welcome back to the Amanda Kaufman show. We're continuing our series on coaches that don't suck. I am excited to invite a fellow CHPC certified high [00:01:00] performance coach Shelly Oswald to the show.

[00:01:03] Hello, Shelly. How are you? I'm good. Hi, Amanda. So good to have you. Why don't you take 30 seconds and introduce yourself to the listeners so that they have an idea of what it is that you do.

[00:01:17] Sure. I'm a business coach and I focus on solopreneurs. I help them understand the business side of business because that's usually, you know, there's so many, opportunities out there [00:01:30] for marketing and for getting skills, but there's not much on the business side of business.

[00:01:35] So that's me.

[00:01:37] Help us unpack that. When you say the business side of business, what do you mean exactly by that?

[00:01:42] I would say, the financial aspects, there are certain tech tools that I work with. So, Shopify is one of the big ones. I'm a QuickBooks online pro advisor.

[00:01:52] I had studied and had been, certified as a profit first professional. I was also a pumpkin plan [00:02:00] strategist. And having 35 years of. business experience, with both brick and mortar and online, there's just so many things that, people think you pop out of the womb with, understanding business and that it's some sort of big failure if you don't get it.

[00:02:15] It's a skill just like everything else that needs support.

[00:02:19] So true. I'm excited to find out that you are a profit first pro that book if you haven't read profit first by Mike Michalowicz, just stop whatever you're reading, [00:02:30] read that first and go back to whatever you were reading before.

[00:02:32] That method literally saved my business a few years ago. It's just like you said, you know, there's so much emphasis in, and in the marketplace. It's both being marketed and consumers are consuming, all this like marketing training and sales training my mission is to help entrepreneurs build a financially healthy business that they actually love doing, so I'm really excited about how you're doing that.

[00:02:57] So Shelly, I'm really curious, What [00:03:00] compelled you into wanting to become a coach that focuses on these things in the first place? You mentioned you had a lot of years of experience, but you could have pivoted, you could have gone another direction. Why do this?

[00:03:13] I've pivoted several different times throughout my life.

[00:03:16] I was really fortunate and the more I go into my journey, the more I understand how fortunate I was. I was raised in a family of entrepreneurs my great grandmother and great grandfather They [00:03:30] were the ultimate entrepreneurs that, that pivoted throughout, you know, you know, the early 1900s and through the depression and, grew the business.

[00:03:41] my great grandmother was a large force in my life. I spent a lot of time with her my grandmother, her daughter had a beauty shop. My mother, she had done different things with, Horses and dogs showing dogs and racing horses. my dad was an accountant and ran [00:04:00] the family business for my great grandmother.

[00:04:02] having been raised in I realized that a lot of people aren't fortunate enough to have that understanding I had to gain skills to step up, when needed into the family business, which, my husband and I ultimately purchased from my great grandmother for me to be able to do that it took skills.

[00:04:20] now getting to this stage of my life it's time for me to give back.

[00:04:25] Yeah, that's really cool. my great grandmother was actually a businesswoman [00:04:30] as well. She ran a school that was established in the early 1900s. She was one of the top students at that school and the previous owner sold it to her she ran it from the 1940s through the 1980s.

[00:04:42] And, you know, you don't hear too often about great grandmothers and business. So that, that's kind of a cool thing we have in common. That's really neat.

[00:04:51] That really is. And it's just, you know, powerful women, because it seems like that's something that's a new thing, but in reality it's [00:05:00] not.

[00:05:01]

[00:05:01] would say maybe not a common thing, but definitely not a new thing. I remember even as I was coming up in my career, my career really did shift quite a bit as soon as I got married. And it wasn't because, I was necessarily the one shifting it. It was the observation of those around me.

[00:05:18] It's like, Oh, she's married now. She's going to have kids anytime now. Oh, she has kids. there's a really great book And she talks about how women are offered so many off ramps financially like [00:05:30] that. oh, it's okay. You got married. Oh, it's okay. You've got kids. Oh, it's okay.

[00:05:34] It's okay. And there's just like all these temptations for off ramps. to your financial future. And, you know, that book really impacted me. So I'm actually really, curious when you're working with solopreneurs, what do you see as the top thing people are really focused on lately in terms of wanting to have more success?

[00:05:54] Like, I'm hearing a lot of overwhelm in general from people that I'm helping, but what [00:06:00] are you hearing on the ground?

[00:06:01] Yeah, it's the overwhelm and, not having any systems and processes in order and everything's just a big scramble. So, you know, that's probably the big key getting a rhythm in order, not having a calendar, not having, any kind of system or process to anything.

[00:06:20] from email and automations, through bookkeeping the whole way through.

[00:06:24] Yeah, it sounds like there's some high performing habits that could [00:06:30] really help a lot of these folks. I am actually really curious about this because I see the same thing in my space.

[00:06:35] You know, I help a lot of online entrepreneurs I have some theories, but I'm really curious about your take. What is it? that leads people to avoid creating systems in the first place? How do they get to this place where every day is a new fire drill every day is really high Anxiety, but like they clearly have a level of success.

[00:06:54] Otherwise, I wouldn't be able to hire you. So what do you think?

[00:06:56] think that that it That when they get to [00:07:00] the point when they're ready to hire me is the fact that, that they have realized that they need to get some, something, something has to give. so they've gotten to a point where, there's a crisis or, they're just out of time.

[00:07:14] They're overwhelmed. They just don't know where they're going to go next. So I think that people get to that because it's like, it's like with any business, you know, most people get into that business because they're good at what they do or they have a skill there's a lot of that, within, especially like the [00:07:30] online coaching space that, that promotes, you have a skill, anybody can do an online course.

[00:07:36] yes, but there's things that go with that. It's not just, marketing. It's not just finding people. you start by, raising awareness and spending your time trying to get clients. by the time you get clients, you have to build a system.

[00:07:50] it's always a catch up instead of saying, okay, these things are going to come at me in the future. I'm going to prepare for them while [00:08:00] things are slower. While I'm looking to start, building, I'm going to start understanding, How to record my transactions in QuickBooks and have basic financials.

[00:08:09] I'm going to, get my emails in order. I'm going to figure out and understand how to do a calendar. I think that there's just not enough discussion about being proactive about business skills there's, so much about the marketing and you can do it, but not enough about the business skills.

[00:08:27] Yeah. and I think My experience has been as well, a [00:08:30] lot of people are just very intimidated by all of it, even the marketing, it's a system, a regular rhythmic system. I think a lot of marketing that gets taught is very like, this one hit wonder, here's this one campaign, or here's this one strategy that could help.

[00:08:45] One of the theories that I have is that people normalize overwhelm, they think, Oh, that's normal. I should be really overwhelmed. Or a second thing that I often hear is like, I'll do it when I'm successful, then I'm [00:09:00] going to go back and I'm going to create the records or, you know, are you hearing kind of this?

[00:09:05] Same thing. And if so, like what, what's your top strategy for somebody to get them like kind of out of that reactive place and into a proactive place?

[00:09:15] I would say, especially, one of the groups that I've worked with has been farms, because I have a farm, I remember us talking about the Roomba and the chickens, and the cows, but especially with the farms, and I think this really goes, it's [00:09:30] a generational kind of thing that.

[00:09:32] there's, the hustle culture that you need to work hard and that working hard is what's going to get you forward, not working smarter. and that's where, especially with the business stuff, people get overwhelmed with not understanding where to start and not understanding.

[00:09:51] That business isn't something, like I said, you just don't pop out of the womb and you're like, you know, you've got business skills. It's something that even if you're a fourth [00:10:00]

[00:10:00] generation, even if you're a

[00:10:02] fourth generation, that's one of the messages even if you come from a family of entrepreneurs, where you see that everybody says that you can do it and you see it being done, there's still so many skills you need to learn there's a different set of skills whenever you, when you purchase a business, that that business usually has some sort of systems and processes already set up. whenever you're starting your own business, you have to create those. So it adds a [00:10:30] whole nother level of complexity.

[00:10:32] That is usually not addressed whenever you hear the rah rah, you can start a business, you can do it, but just do it with your eyes wide open that it's absolutely crucial for you to be sustainable in the long run. it's absolutely crucial for you to get those, basic business skills and get, those systems and processes in order it's so much more than marketing and being good at what you do.

[00:10:58] I'm really curious, Shelly, What [00:11:00] role has coaching played for you in your journey?

[00:11:04] Okay. Well, the coaching is actually a little bit newer. Part of my journey.

[00:11:09] consulting has been more of it, up until this point, so coaching was a very, big pivot for me because I realized that I didn't want to do the work for anybody anymore, which was the consulting. I wanted to empower people to be able to do the work on their own.

[00:11:26] I felt that I was, that I was taking, I was [00:11:30] taking, the responsibility. And, and also I, I realized that I was taking the responsibility and I was also, you know, not empowering people. I was actually disempowering them by doing it for them. when I came to that realization, it became a pivot to a different place.

[00:11:47] I love that. I love, I love how you're like thinking in the longterm about, about what's good for the client. You know, it's interesting you bring that up because I had a 10 year consulting background [00:12:00] as well. I found that the coaching skills really help people take, all of the process documentation we did, all the tools we did, all the tech that we did, and it helped them own.

[00:12:10] Their own implementation for their own good of what they wanted to do, because I was shifting how I was, communicating and managing with change that it was more left in their court. Right. So that's Really cool. So, what have you found to be maybe some of The surprises along the way as you've brought, coaching into the fold, has [00:12:30] it gone completely as you thought it would, or have there been any surprises?

[00:12:34] at this point in time, it's been pretty much, as I expected, I feel so much better about, watching my clients progress. it's just been really fulfilling in that respect.

[00:12:45] That's really cool. So Shelly, I love asking this in the segment is, what are the three things that you think help a coach not to suck?

[00:12:55] that's a good question. I think that the first thing is that you need to [00:13:00] ask the hard questions.

[00:13:02] go there.

[00:13:03] you need to have the empathy for the person that you're working with, but you need to hold them accountable.

[00:13:08] And, I think The third thing is you need to be organized.

[00:13:14] That's so good. I actually just did another podcast interview with someone and they said basically the same thing especially that third point about the organization.

[00:13:23] we were talking about what it means to go pro I like to tell people the coaching industry is a super low barrier [00:13:30] to entry and a super high barrier to success. Because the success, it requires you to, I love, I love systems. I'm like totally biased there, but, you know, even, even with marketing and sales, one of the big costly lessons I've learned is you can have the best marketing in the world, but if you don't have a great system for relational followup that is authentic and really connected and, you know, helpful, then it doesn't really matter what you do.

[00:13:58] in regard to marketing [00:14:00] and sales, you could be the most diehard committed salesperson. But if you don't have marketing to back you up to showcase what your business is doing, you're going to find sales is always an uphill climb. the trouble I got into, I thought I made it, back in 2018, I was selling at a high level and I, and I had all these clients and they were amazing and I was having this awesome experience, but I needed to learn what I learned in profit first around systemized decision making regarding [00:14:30] finances.

[00:14:30] because I was so interested in growth and expansion and people were giving me advice all the time about, having more team and having more systems. before I knew it, my PNL was completely screwed up, if people wanted to follow you or catch up with you, what's the best way for them to do that?

[00:14:46] probably the best right now is on Instagram at I am Shelly Oswald S H E L L Y O S W A L D.

[00:14:57] what's one thing that you're really working on right now [00:15:00] that you're excited about?

[00:15:03] My app, my Kajabi app.

[00:15:08] Tell us about this app before we go. What are you building?

[00:15:12] Okay, so on Kajabi you can have a custom branded app and it makes the integration between community and the courses very easy because everything's on that app.

[00:15:25] So you can listen to everything on the go. you can actually [00:15:30] Communicate through the community, right from the app. for me, I find it social media is like a huge time sucks. So the least amount of time I can spend there is better. Whenever you have to remember all these different logins in order to go in to, participate in a community.

[00:15:47] I found that that's been a challenge. I'm in the middle of building that right now. I've got my Google developers license, my Apple developers license, and I'm, putting the test course on hopefully. Within a [00:16:00] month or so that'll be launched.

[00:16:02] That sounds like a really good enhancement for your community.

[00:16:04] Thank you. Well, listener, thank you so much for joining us for another episode do us a favor, go ahead and leave a five star review for us. along with what you loved about it and subscribe so you don't miss the next one. if you've got a friend or two who is in the midst of business building, forward this episode to them so they can get some ideas and insights on how to get unstuck.

[00:16:27] We'll see you next time.