The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Leadership/Mission Driven Business
Mission Driven Business artwork

How to Make Smarter Business Decisions with Dawn Kennedy

Mission Driven Business · 2026-08-25 · 46 min

0:00--:--

Key moments - from our scoring

Substance score

62 / 100

Five dimensions, 20 points each

Insight Density13 / 20
Originality12 / 20
Guest Caliber16 / 20
Specificity & Evidence11 / 20
Conversational Craft10 / 20

This episode features Dawn Kennedy, author and creator of Strategic Intelligence on Main Street, discussing how entrepreneurs can make smarter decisions when facing incomplete information and limited resources. Rather than conventional wisdom about business planning and execution, Kennedy draws from her background in military capabilities development, enterprise consulting, and hard-earned lessons from losing her first company (Unique Consulting LLC) to an unexpected crisis in 2013. She now applies sophisticated decision frameworks designed for Fortune 500 companies to small and mid-sized businesses through her consulting work and her own coffee roasting business, Convoy Road Coffee Roasters. Kennedy challenges entrepreneurs to examine often-hidden dimensions of business decisions: human capacity and life circumstances, cash flow requirements for survival, the risks being assumed, and how to hold decisions long enough to see evidence while remaining flexible to feedback. She illustrates with real examples - a restaurant deciding to bounce a check rather than close temporarily, COVID-era SBA loan holders facing asset liens they didn't understand - showing how pre-execution clarity prevents costly mistakes. Her frameworks help founders distinguish between decisions that are genuinely unwise versus those that simply require patience and iteration.

Key takeaways

  • →Before making major business decisions, map your true cash floor - the minimum recurring revenue needed to keep doors open - rather than just evaluating interest rates or loan terms.
  • →Evaluate your human capacity alongside financial capacity: life events, family circumstances, and personal bandwidth matter as much as widget production or work hours in determining whether to expand or take on obligations.
  • →Hold decisions long enough to see evidence of working or not working, rather than abandoning them after two weeks of crickets or stubbornly wedging a rejected idea into the market despite feedback.
  • →The 70% of entrepreneurs without formal business training often lack understanding of hidden risks like key person insurance, SBA loan asset liens, and tax liens on personal property when business fails.
  • →Mission-driven businesses succeed when they prioritize loving their team more than customers and customers more than products, ensuring the business remains durable if owners aren't present.

Guests

Dawn Kennedy

Topics in this episode

Key person insuranceStrategic Intelligence on Main StreetUnique Consulting LLCConvoy Road Coffee Roasterscash floor conceptSBA emergency loans and asset lienscottage food lawsdecision frameworks for small businesscapacity planning (human and operational)financial decision tools

Questions this episode answers

What should I do if my business can't pay a bill on time but needs to keep operating?

Rather than closing or waiting for cash to arrive before paying bills, you may need to knowingly overdraft your bank account if revenue is coming within days - accepting a small overdraft fee to keep your revenue engine running is sometimes smarter than the shutdown that conventional wisdom suggests.

What is a cash floor and why does it matter more than loan terms?

Your cash floor is the minimum recurring revenue you must generate to keep your doors open and continue operations; understanding this number is more important than focusing on interest rates or loan terms when deciding whether to borrow.

Why do second and third-time founders have better success rates?

Founders who have already failed or struggled in previous ventures have experienced real consequences and learned lessons that formal business training cannot teach, making them more cautious and strategic in their next venture.

How long should I stick with a business decision before changing course?

You should hold a decision long enough to see actual evidence of whether it's working or not working, avoiding both the trap of abandoning ideas too quickly (before adoption cycles mature) and the trap of stubbornly persisting with rejected ideas despite clear feedback.

What hidden risks should entrepreneurs understand before starting a business?

Common hidden risks include key person insurance gaps, exclusionary periods for Social Security benefits when catastrophically injured, SBA loan asset liens that prevent selling business assets, and IRS liens on personal property when business debt remains unpaid.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

13 / 20

The episode contains valuable operational insights - particularly around decision frameworks, capacity planning, and the CLARITY method - but is diluted by significant throat-clearing, repetition, and conversational padding. The core material on pre-execution decision-making and the distinction between known/unknown risks is solid, but the host and guest spend considerable time on thematic setup and validation rather than drilling into specifics.

The very first thing...is your capacity. And I don't just mean your capacity for how many widgets can you produce or how many hours can you work and how many things. There's other capacity. There's the real human side of business
Well, have you raised enough of your cash floor by contract or repeatable business that you can absorb a loan payment to take that capital on prior to returning on your investment?

Originality

12 / 20

The episode presents a contrarian angle on conventional business wisdom (e.g., bouncing a check strategically to keep cash flow alive; questioning EBITDA over cash; reframing when to hold vs. pivot decisions), which is refreshing. However, the core frameworks - capacity planning, cash-flow focus, decision checkpoints - are not entirely novel, and much of the originality is diluted by relying on familiar entrepreneurial tropes (build-measure-learn, persistence vs. flexibility).

My advice literally was, you're going to have to swallow your pride and you're going to have to bounce a check to the bank...if you don't open your doors today, you have no chance of making revenue this week.
I don't care. What is your cash? Right. What is your lead time?...I have never...had anybody come up to me and say, wait, wait, what about our amortization schedule? That's the A in ebitda.

Guest Caliber

16 / 20

Dawn Kennedy is a credible practitioner with legitimate multi-domain experience: military capability planning, enterprise consulting, law, and hands-on entrepreneurship. She has lived through catastrophic business failure and learned from it, then applied those lessons to a second venture (Convoy Road Coffee) that is now in year six and scaling. Her combination of large-org rigor and small-business ground truth is rare and relevant. However, she is not a household name or mega-scale operator, which prevents a higher score.

I have a background in, uh, capabilities development for the military...I was also doing, uh, Enterprise Consulting, Fortune 500 stuff for a while there too.
November 1st of 2013, my husband had a near fatal ACC and fell 18ft off a ladder...we were staring at about $77,000 in business debt, plus an IRS lien on our house

Specificity & Evidence

11 / 20

The episode lacks sufficient concrete data, metrics, and timelines. While Kennedy provides some specific examples (the $77k debt, Nov 1 2013 accident, $375k contract, month-over-month doubling in the coffee business, $2.4M company example), most of the decision framework discussion remains abstract and theoretical. Few named companies, no real financial numbers to anchor claims, and the coffee roastery story, while illustrative, is anecdotal rather than data-driven. The host rarely pushes for specifics.

Almost a quarter million in two years...contracts for 375,000 starting January 1st of 2014...staring at about $77,000 in business debt, plus an IRS lien
We doubled in month two, and then we doubled again in month three.

Conversational Craft

10 / 20

Host Brian Thompson asks competent setup questions but rarely pushes back, probe deeper, or challenge Kennedy's claims. The conversation is warm and validating but lacks the friction that would deepen insight. Thompson asks few follow-ups on specifics (e.g., how exactly does the CLARITY framework differ from standard decision-making frameworks in measurable terms?) and lets Kennedy control pacing and abstraction level. The host spends time relating to her own experience rather than extracting more rigor.

Yeah, I love that. I don't think I've ever heard it said that way, but it makes so much sense
Yeah, I'd love to hear more about the decision framework because you said we got to a decision point.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A76%
  • Speaker B24%

Most-used words

decision34coffee21back18businesses17mission15decisions15conversation14trying14entrepreneurs13tools13sure13long13point12making11love11everybody11

Episode notes

Most entrepreneurs make major business decisions without a reliable framework to guide them. In this episode, Brian Thompson sits down with Dawn Kennedy, attorney, entrepreneur, and author of Before You Decide, to explore the pre-decision tools she developed after losing her first business overnight and spending years translating enterprise-level decision frameworks for small and mid-sized business owners. Dawn's story is both practical and deeply personal. After her husband suffered a catastrophic accident in 2013 that ended their consulting business instantly, she realized how much she did not know. What came next was decades of developing decision tools that help entrepreneurs see the full picture before they say yes, no, or not yet.

Full transcript

46 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Hello.

Speaker B: Welcome to the Mission Driven Business Podcast. I'm your host, Brian Thompson, an attorney, certified financial planner, and founder of a financial planning firm that serves LGBTQ entrepreneurs. I, uh, created this podcast to help mission driven entrepreneurs build businesses that are both profitable and meaningful. On the show, you'll hear conversations from diverse entrepreneurs and experts who support small businesses in many, many ways. We'll talk about marketing, money, strategy, mindset, and what it really takes to build a business that aligns with your values and supports the life that you want. So whether you're just getting started or growing an established business, you're in the right place. Hey, everyone. Welcome back to the Mission Driven Business Podcast. I'm, um, your host, Brian Thompson, and today I'm talking with Don Kennedy, an author, business operator, strategist, and the creator of Strategic Intelligence on Main Street, a decision making discipline designed to help entrepreneurs and business leaders make consequential choices when time is limited, information is incomplete, and real resources are on the line. Dawn's perspective is especially interesting because it comes from both sides of the equation. Her background includes military capability, planning, enterprise intelligence, consulting, and law. But she's also an entrepreneur who has experienced firsthand what happens when business plans collide with circumstances you never saw coming. After a devastating accident abruptly, uh, ended one of the businesses she built with her husband, dawn began translating the decision making tools she had used in larger organizations into practical frameworks for small and mid sized businesses. Today, she also puts those frameworks into practice as co founder and CEO of Convoy Road Coffee Roasters. In our conversation, we talk about why the visible decision is rarely the whole decision. How to evaluate what your business can actually carry before saying yes, and why following a conventional business wisdom isn't always the smartest move. We also explore capacity, cash flow, risk, knowing when to stick with a decision and when to change course, and the importance of understanding the things you don't yet know. You. You don't know. If you ever found yourself wondering, should I hire? Should I borrow? Should I expand? Should I keep going or change course? This conversation will give you a much more thoughtful way to approach the answer. So with that, here's my conversation with Don. Hey, Don. Welcome to the Mission Driven Business Podcast.

Speaker A: Thank you so much for having me, Brian. I'm looking forward to our conversation.

Speaker B: Me too. We got to talk on your podcast and it was such a great conversation that I was so excited to have you on mine. So I'm, um, excited to talk, talk, share with my listeners about frameworks, decision frameworks, and how to build a successful Thriving business. Um, but before we get into that, let's start with a question that we always do. How would you describe a mission driven business?

Speaker A: So the mission driven business has I think, two components. One is a real clear understanding of what they're designed to do, what they are going forward and bringing into the world with its unique DNA. Because a mission driven business can look like other businesses in the industry, but it will have its own unique story. And then the second component of that is making sure that we are aligning our mission so that we love our customers more than our product and service and we love our team more than our customers. Because then not only are we following a clear mission, but we're making sure that the priorities of how that mission is implemented is supporting durability, longevity and being able to continue operating if the owner, founder, leaders aren't in the room.

Speaker B: Yeah, I love that. I don't think I've ever heard it said that way, but it makes so much sense when you not only talking about the impact, but how, how you get there, making sure that that is aligned with what you're trying to accomplish. I love that.

Speaker A: I appreciate that. Yeah, I think sometimes, um, we get to the place where, well, we'll just figure it out or we maybe take some shortcuts and you know, sometimes we, we justify why we did the thing we did after. Right. So the ends justify the means, which I don't, I don't necessarily agree with. I think that the means have to be aligned with the ends that you're reaching for. And that means doing good business, being ethical over communicating when you have to. You know, um, it doesn't, it doesn't mean rolling over and showing your belly, if you will, but it does mean that every step you is taken with the full voluntary willingness to carry what you're doing.

Speaker B: Yeah. And I think that also entails then knowing what you're doing and knowing why you want to do it. I feel like I come to a lot of entrepreneurs who get into the business because they're good at something and they've never really thought about their mission, their vision, their values, and how those will then dictate the decisions that we make.

Speaker A: Yes. So, you know, a lot of times we do have these passion led businesses which are incredible, but understanding that, you know, passion alone is not going to probably cause you to become durable. Uh, and it's, it's interesting, I heard this statistic actually from another business owner not that long ago. Only 30% of entrepreneurs actually have any real practical business training before they open 30%. Yeah. So there's 70% of people that maybe worked in corporate, maybe they have managerial experience, maybe they have, you know, experience in the industry that they wanted to break away and start their own thing. And that's fantastic. But operational or management experience is not the same as saying you carry all the payroll, you carry the risk, you carry those decisions. And, you know, they. The fundamental business training that people get, in a lot of cases, even if they come out with an mba, it's going to be theoretical because the boots on the ground and that, you know, getting your butt handed to you a few times is really the lesson. Um, and, you know, we can't fault people for not having formal business training, if even with formal business training, you still don't necessarily hit the ground understanding what you're supposed to be, be doing. And right, the really cool thing, or I guess if you want to think about it, is the second and the third and the fourth time founders that actually have the best chance for success when they launch a new idea because they have had their butts handed to them probably early on in their other ventures, right?

Speaker B: It's that concept of build, measure, learn, right? You have to do things, you have to try things, you have to iterate in, uh, order to really be successful in your business. It still entails knowing the foundation, right? The mission, the vision, the values, but then just trying things and trying to figure it out. Um, which we will talk about, right? We will talk about mindsets and shifts, about how to do that. But before we get there, I want to hear a little bit about your background, how your business, uh, how you started your business. It's such an interesting concept. Uh, so tell us a little bit about Don.

Speaker A: Okay, so I'm going to go back to actually 2011, 2012, 2013. Um, I have a background in, uh, capabilities development for the military. Meaning look at the capability gap. Is there a way to solve it without buying another piece of equipment? Oh, it's not. We have to enter into what we call the acquisition cycle, and it's its own stuff. Ah. I was also doing, uh, Enterprise Consulting, Fortune 500 stuff for a while there too. They have a lot of the decision tools and things around. Where do we put our money? How do we reduce our risk? Well, in 2011, um, my husband and I started a consulting company called Unique Consulting llc. And we did really well because we both had backgrounds. I had a project management background, and then he also had a background in experimentation, design. So if you can imagine trying to figure out if Something might be a good market fit. You know, that, that's kind of a good skill set that plays off each other for sure. However, as well as we were doing on, uh, November, uh, first of 2013, my husband had a near fatal ACC and fell 18ft off a ladder at a training facility, landed on his head. Four skull fractures, wheelchair, the whole thing. And in that instant moment, even though we had gone to the SBA in spore we had given our business plans, everybody said, yes, this looks great. We had revenue of almost a, uh, quarter million in two years. And then we had contracts for 375,000 starting January 1st of 2014. Um, as of November 1st, 2013, there was no more company. It was gone in, in three seconds. And the thing that hit me the most about it was what I did not know. So I didn't know what key man insurance was. I did not know that there's an exclusionary period for things like Social Security when you're catastrophically injured. I did not know about the protective measures that we could have taken inside our business. And so we were staring at about $77,000 in business debt, plus an IRS lien on our house for, uh, unpaid self employment taxes. Because even though you are catastrophically disabled and deemed uncollectible, you own a house, they're going to attach your house. That's just the reality. Don't necessarily fault them for it, but it would have been nice to kind of understand that and I had to learn all of that on the fly. So, you know, years and years later, we paid everything off. Took about 39 months working a bunch of different jobs. Side hust went back to work for the military for a while and then, uh, started consulting as well and sort of stabilizing things, kind of licking our wounds, getting it all figured out. I started doing what I now call strategic intelligence on Main Street. I didn't quite know what it was back then, but I was like translating some of these decision frameworks that we use to reduce risk at enterprise for some of the smaller businesses. And I was consulting at the time and I had uh, a couple of businesses that came to me because they were basically in distress. And it's like, can you help us make the decision? You know, what do we focus on? Do we need to close? You know, and again, because I had been a business owner in crisis and I had ultimately lost my business, now they were really willing to sit down with me and over the next, I would say, seven, eight years, all of these tools developed about, you know, decisions on Market fit decisions on, you know, financial cash floor, like what you absolutely have to make to keep your doors open, to keep generating money. And some of the advice and things that I came up with was pretty counter to sort of the, the traditional wisdom. So I'll just give you a brief example. I was working with a restaurant at one time that ended up uncovering a big chunk of embezzlement, um, from, from a person. And when that happens and you know, all those things, they're in the collection, notices started and stuff. And I, uh, get a frantic phone call because they get a disconnect notice for the water. And they had some structural things financially where they didn't have the cash in the bank that day. And my advice literally was, you're going to have to swallow your pride and you're going to have to bounce a check to the bank. The money will be there in two days. You're going to take that, whatever the overdraft fee was, $35, 38, whatever it was. I said, but if you don't open your doors today, you have no chance of making revenue this week. So we're not going to wait and pay the disconnect notice and do what everybody else would have said, conventional wisdom. Oh, you clear that up and then you reopen. I was like, no, you have to be able to keep that, that revenue engine going. We're going to bounce a check to the bank, knowingly knowing the consequences. Oh, well, knowing that this is going to cost you money. Um, but if you don't do that, you cannot continue to operate. And the back end side of, you know, the embezzlement things, as unfortunate as that was, it again, was one of these things where, you know, trust was given, maybe where it was unearned, resumes were read rather than character. And guess what, again, as business owners, we all do it right? So as that wisdom was kind of coming out, I had people who were referring businesses to me post Covid for full disclosure. I'm also an attorney. And so they would, they would, you know, say, hey, they have these huge, you know, SBA emergency loans, those idle loans, and they can't make the payments on them. And, you know, what is the reality of this? And based on the amount of the money of the loan, the SBA takes a lien on all the business assets. So it's like, you can't sell the trucks. You can't, you know, and so there was a lot of navigation there as well, where the conventional wisdom of, well, liquidate everything, pay that loan off you know, there's, there's legal pieces to that again, that business owners were not aware of when they were trying to survive during the pandemic.

Speaker B: Yeah.

Speaker A: So that translation of tools and, and the realities of what people think they know, but they don't really know, uh, has created sort of this niche now of what I call pre execution decision tools. So that you are fully aware of what the realities are, what we're volunteering to carry. Uh, and you know, we try to really uncover all the blind spots before somebody says yay. Verily, verily, we're going to go forth and do this thing.

Speaker B: Yeah. And that's such an important thing to think about when you're starting a business. So you are. Because there's a lot of things that we, we don't know. We don't know. And um, having someone with your expertise and your experience and the story of how you got in there, wow, that's so. Also so powerful. Um, you know, I, I can see why you were talking about two third and fourth generation business owners being so successful because of, you're an example of that, of like having to start, stop something happen and then starting again and sort of figuring out how to get your feet back under you and how to make it work. And uh, it's such an inspiration. So I love hearing that, those stories. Um, so let's talk about this pre decision framework. What do business owners need to be thinking about before they start their business?

Speaker A: Yeah, uh, the very first thing. Because again, mission and vision. There's tons and tons of books that talk about all of those pieces. But things that we don't necessarily always talk about clearly are things like your capacity. And I don't just mean your capacity for how many widgets can you produce or how many hours can you work and how many things. There's other capacity. There's the real human side of business that for some reason as entrepreneurs we're sort of expected to either go all in and sort of check out on this side or to try to find that work life balance. And I have been involved in enough. I'm going to call partner dissolutions. Right where it looked great on paper. We're going to go forward, we're going to do this and then you sit down and you start asking the questions, well, what changed over the last quarter? Oh, my daughter is pregnant and now we're going to have this grandbaby. Okay, so should we open a second location in that quarter when you know the human realities of your, your desire to be there? Um, you Know, and, and we don't necessarily look at those things with the same level of scrutiny that we look at cash flow, right? Or, you know, or marketing, sales, product, market. And you know, the other thing is once we make a decision, and I think this also goes to mindset, is the conventional wisdom is, well, you made the decision, you have to stick with it until you see it through, instead of saying you made the decision and you're going to hold in long enough to see the evidence of it working or not working, right? So it, it's almost like there's this pendulum, right? So you put it out in the market, you get crickets for two weeks, you don't understand the adoption cycle of, of new and great ideas. And so you pull it back. And so the people that were preparing to buy, they were looking for the social proof that it's, they no longer have the opportunity to do that. Then you're sitting there and instead of going, well, maybe we didn't leave it out there long enough. The other thing is, you leave it out there and even though you're getting feedback, you know, you're sold into your idea. And so you're continuing to try to wedge your idea into the market where, you know, maybe, maybe it's the wrong delivery style, maybe people are looking for it a different way, but you're so convinced that you're your decision, like the way you're going to do this is the absolute best way, the only way. And I think those two edges of the pendulum are where businesses tend to get in trouble, right?

Speaker B: You have to be in the middle. You have to be learn how to sit in that little gray area of not knowing and being open to the feedback, the iteration, the ability to change your mind. Um, I think that's one of the biggest developments as an entrepreneur that I had to make. Um, I'm a very rigid, structured person. I like routine. I like knowing what's going to happen. And that's just not how business works. Uh, you have to try things, see, uh, how they fit and find, uh, that balance of putting it out there long enough but not putting it out there too long to where you're not, uh, changing and getting that feedback. That's such a great note for people who are getting in the business and think it's going to go one way, right?

Speaker A: You.

Speaker B: I started this business 10 years ago thinking it was going to be something, and it's now something different, and I love it. Um, and I think a part of that is just being willing to change with, uh, and as you evolve and understand, too. Because I think when you're talking about capacity, it all goes back to this internal understanding of yourself saying, how much capacity do I want? What do I want this to be? Mission, vision and values. Uh, how do I fit in? Our last conversation was about sort of the person in the business, right? How do you. You separate those two or how do you integrate those two? Um, so I think it still also goes back to, what do you want? What are you trying to build? What are you trying to do?

Speaker A: Yeah, exactly. What you're trying to build and what you're trying to do. So in 2021, in January 21st, we actually started another company. So my husband is a huge coffee guy. I mean, ridiculously sold out to coffee. He's the guy that'll happily come up to me with a little bag and be like, hey, I found this xyz, Jamaican Blue Mountain, whatever from this roaster. I was like, oh, okay, okay. Um, how much was that a pound? He's like, well, you know, $75 a pound. You're like, oh, okay. I hope you enjoy it. Right. Um. And he was stationed in Panama in the late 80s, and he realized that he didn't like mess hall coffee nearly as much as he liked the coffee being grown in the region. So he's been chasing coffee for over, I don't know, 30 years. Well, I made the mistake. I call it the mistake now, but I also call it the opportunity. I got him a little tabletop coffee roaster and some raw coffee beans for Christmas in 2020. It was kind of a hobby he was looking at wanting to get into. And within just a few weeks, I was like, wow, okay. He really understands coffee, how to roast coffee, what it means, doing the research like that, 30 years of hobby, playing with it and whatever turned into it. Uh, he's got a palette, he's got a gift. So about three weeks in, I bet him a dollar, and I said, I bet you a dollar I can sell this freshly roasted coffee on Facebook. He's like, chick, you're nuts. And I'm like, okay, I'm nuts, but we're going to do it anyway. That First Post sold 11 bags, and we had like four available. And I was like, oh, okay, maybe there's something here. And, you know, again, being a, uh, risk averse lawyer, I had already looked up cottage food laws. Whether or not you could sell what you roasted. What does the USDA labeling need to look like? You know, this, this product is home produced. So anybody who's ever like, Baked banana bread and gone to a market. Understands that there are certain laws that, where the government says, yeah, you know, these are very low risk foods. And you know, you obviously have to keep your kitchen clean and stuff. But there's a, uh, low bar to entry. And so coffee is one of those things that you can roast and you can sell. And it's a very low bar to entry. And then we realized that we doubled in month two, and then we doubled again in month three. And then I'm looking at it in April. So we, we sold our first bags in January. And this was also during the pandemic. So just a side note, anecdote. We were doing, you know, delivery in the driveway, right? We could walk out with paper bag and hand it to them. They'd hand us the cash and we come back in and at one point we're like, we should probably tell the sheriff what we're doing. Just so they know we don't have any sign ins. We don't really exist yet. You know, we should just let them know that that's, that's coffee going out there in those paper bags. We didn't have a logo yet. We didn't have uh, packaging yet. We, I mean we were looking at it and you know, the decision point came so April of the same year. The decision was, is this just going to continue to be like a fun little hobby business or something? Or is this something you'd really like to pursue? And he's like, oh, I really want to pursue it. And I said, okay. So we ended up leasing our first commercial roaster because I was so afraid that if it didn't work, I'd be on the hook for all these payments. And then to release, I was like, I figure I could write off all the lease payments. I won't be able to get the depreciation later, but so what, at least I feel like I'm somewhat protected. And so after losing that first business, which was still, you know, in the back of your mind, you know, we, we made decisions a little differently and we scaled a little bit differently. But we are, we're now in year six, right? 20, 26. We started 21 and we are adding a custom blending lab. We won grants from the state. We've been doing our expansion. We are in a, ah, number of local grocery stores. We now have a retail uptown that we, we share with another, another business. But each one of those steps along the line I think was maybe over analyzed through my decision frameworks. Um, but we were willing this time at Least to take those steps and make those risks. As long as they were a little more calculated. We were a, um, much smarter business going in again that second business, third business, fourth business. Your optimism is very easily tempered by the bad things that happened to you in the past.

Speaker B: Yeah, I'd love to hear more about the decision framework because you said we got to a decision point. I want to know what that point looks like. How do you know it's the decision point? How do you know it's time to jump in or jump out or tell me about the decision making up through that point?

Speaker A: Yeah, so the decision tools that I have actually cover different aspects of the business. So there's financial decision tools like do we take the loan? Well, most of the time the thing I hear back is, well, what's the interest rate and what are the terms? And instead I'm asking, well, have you raised enough of your cash floor by contract or repeatable business that you can absorb a loan payment to take that capital on prior to returning on your investment? Right. So prior you make the investment, let's say in employees, what is the training time for that? Are you going to be able to carry those things without putting pressure on the cash in the business? Then I have market tools, market tools about where's your industry going? What is your audience delivery, focus and process? How are we looking at what may be evolving or what people may be asking for? And then how do we evaluate those things? I have a framework called clarity. And basically it's because, uh, typically people say, well, you should do this planning thing. And EBITDA is what? A lot of times consultants will come down and say, let's say, well, what are your earnings? And I'll look at that and say, I don't care. What is your cash? Right. What is your lead time? So the L is lead time. I have never, in all the years I've worked with companies, ever had anybody come up to me and say, wait, wait, what about our amortization schedule? That's the A and ebitda. And I'm like, I don't think anybody's actually ever asked me that question. And it kind of makes me wonder why we're using those tools. For sure, that they're not great. But I mean, I'm more worried about cash. I'm worried about lead time. I'm worried about whether the market's receiving it. A is for activation. I'm worried about T trouble spots. I'm worried about how long we're going to hold this decision before we have to check our assumptions and conditions. And then we have some waiting things on that. This year maybe, um, you know, there's uh, one particular condition that needs to weigh a little heavier, like the Grandbaby example that may not have had to be weighed two years ago or next year or the year after. So what I like to bring these tools in to do is to say two similarly situated businesses, because they're unique, can have two different sets of risk profiles. They can have two separate, you, um, know, training programs. They could have two different things. And I give.

Speaker B: Even if they're the same business.

Speaker A: Right, yeah, I'll get a hold of the book. But I do give an example in the book here where, you know, a, a $2.4 million company, the same exact number of employees being around for the same amount of time, and all those things may have an opportunity like, hey, the industry is moving this way. We need a $60,000 piece of equipment investment. Well, okay, does that include things like the installation, the tooling time, the training time, the things? Is that really a $60,000, uh, investment or is it actually a lot more?

Speaker B: Right.

Speaker A: And then, you know, maybe in business A, they have somebody who has some experience with that kind of tool and is interested in learning it, and maybe in business B, they don't really have somebody. So it all falls to the owner to, to implement all that and get it in. Does that change the decision if one says yes and the other one says no or not yet? Could they both be sound decisions?

Speaker B: Right.

Speaker A: In the companies and building a more durable framework, um, for judgment transfer later? Because if you understand what went into and why you made the decision decision, it's easier to train your layers as you grow to, hey, these are our sacred cows. These are not our sacred cows. Right? These are, these were sacred cows two years ago, but we've grown past them or whatever. And it allows for that level of flexibility and judgment transfer that I think is widely missing in the small and medium business space. Not, not because it's not important, but because if you read most of the books that are written for small and mid sized businesses, especially about things like operations, they will, they will talk about SOPs and they'll talk about execution and they'll talk about using project management tools and timelines and you know, check this weekly, check this monthly, but they don't talk about what actually needs to be transferred so that you can step back and you can keep kind of that 50,000 foot view as you grow so that you can continue to make those durable decisions. Because Once you get to the place where you're carrying payroll and all these responsibilities, you're not deciding for yourself anymore.

Speaker B: Right.

Speaker A: You now have uh, taken on an amazing responsibility and a beautiful obligation to take care of your employees as well. And then stewardship becomes another decision. Um, point. And there's a, there's a book called Unreasonable Hospitality, uh, by Will Goudreau and he talks about that. You know, sometimes I have to make decisions for the business. Not everyone will like them, but it's for the business to protect everybody here. And that's pretty powerful statement when you make it right.

Speaker B: I, I think it's, it's absolutely helpful then to have this framework that you can use to go back to and say, all right, so how do, how do I actually make these decisions? Because that's really uh, a sticking point for a lot of entrepreneurs is they, they have these questions, they know the questions asked, but they don't know how to then think about the framework. And um, one thing that you said that really resonated with me is that there are frameworks for small and medium sized businesses that don't apply to everyone. So you need to think about your specific business because it is unique and because you have a unique perspective and unique uh, tools and capacity and talent for your business and not just sort of go with this guidance of this is what other businesses do. So this is how we're going to do it.

Speaker A: Yeah, I think, um, I think especially with the rise of digital media and the rise of uh, the hacks and the shortcuts and uh, do this one thing, double your email list overnight or whatever it is. And I'm not saying that that stuff is maybe, you know, bad or wrong or doesn't work, but it probably doesn't work for everyone the exact same way. And I think sometimes we have actually sort of put the due diligence in our, in our back of our heads because we want to be that unicorn. We want to be, you know, we, we grew to $11 million in, in just 30 days. And it's like, okay, in the book I actually discuss where the term unicorn came from. And it actually came from some venture backed businesses. Uh, and it explains why math works that you know, you, you get that one in a however many shots and you know, everybody kind of glommed onto that, all the business media stuff too. Because don't we all want to be rare? Don't we all want to be, don't we all want to be winners? Don't we all want to be unicorns? Right. And actually, the best thing that you can do is build your business so that I would say at least 90% of it is just boring every day. And every day it's like rinse and repeat. And it's rinse and repeat. Are you going to have issues? Yes, I am. Right now in a commodity business where coffee prices have spiked. It's all over the news. Uh, supply chains have been just kind of a nightmare. And, you know, a little over a year ago, I sat down and went, you know, isn't that interesting? I never sat down and said, huh? Have you considered the geopolitical implications of the business you're getting into? And I'm like, no, absolutely not. I did. Never occurred to me that some companies, some countries don't have contracts with my suppliers anymore or they're making, you know, contracts over here. It. It was not something that even, even occurred to me. Why? Well, coffee is available seven days a week, 365. And, uh, just about any store you walk into. And a specialty roaster, you know, we import coffee through certain suppliers a specific way. But if there is a country that they can't get a contract with because maybe there was a drought or maybe there was something else that does kind of roll down and affect us, uh, it definitely makes it fun and exciting, but it is. It is not something even that I knew was a, uh, variable when we got into this and got started. And the more that we start to learn those variables and we're in it, like I said, we bump our knees and we skin our elbows. I never expected to have a USDA license and have to go to a food safety certification, you know, thing. I never planned on running a restaurant. And we're a roastery. We're primarily manufacturing, but those are the licenses and the rules that we're required to follow. So you, you know, you swallow your pride and you go, okay, I'm gonna go. I'm gonna go take this very expensive class, and I'm gonna go take these exams. And. And I'm going to understand that 95% of the time, I will not be receiving oysters on the half shell at 41 degrees. Um, but, you know, it's. It's part of what you're obligated to do as well when you make those next steps. And maybe you do need to find a mentor. Maybe you do need to take a course. Maybe there is something that you see as a gap that's required for you to stay competitive, and we have to be willing to do those things as much as we might. You know, it was like I, I didn't plan on taking that course, but I had to, I was happy to do it. Um, at the time I was thinking to myself, I hope I can remember all these things because I'm not in the restaurant every day, you know, I'm not, that's not my thing. So when I went into exam, I'm like, please help me remember, you know, the, the, the temperature of chicken versus the temperature of beef versus soup. Because all those things were on the exam.

Speaker B: Yeah. And you're, you're taking the next steps in service of that business. Right. So you still know what the next step is. And I think that's also an important point to know that, um, you have a direction but you don't necessarily, you may not know the next steps and it's just trying to figure out, build, measure, learn, iterate, um, until you figure out the next step and maybe something that you never thought you could do or never thought you would have to do, but something that's going to be in service of the final goal and where you're trying to get right and

Speaker A: you have to be willing to kind of ask the questions. That's, I think the other thing, um, there's a lot of, of I'm going to call non entrepreneur pressure that gets put on entrepreneurs sometimes like just take the line of credit or this is your big break or oh, congratulations, we're all behind you. But at the end of the day, they're not actually carrying what that decision requires and they're not staring, you know, at the things at 2 o' clock in the morning. And I think sometimes when we listen to non entrepreneurs because we want to believe that everybody is just as invested in our success as we are, but the reality is, you know, stopping and making sure you fully understand what's involved has been sort of downplayed as like push through your fear. Right. You know, the more you stall the decision, the more you're going to lose the opportunity or whatever it is. And again, I come from a place where there's no villains here. This is, well meaning this has been out there. I just, I believe it's incomplete. And what I'm trying to do now I think is close the loop of that and say you can have all of that as well, but at the end of the day, you are the one who has to carry whatever it is you say yes to, no to or not yet.

Speaker B: Yeah. And the book is called before you decide. Right. Um, but it sounds like a lot of these Decisions. A lot of these decisions are also happening as you're running the business. Is that right?

Speaker A: Yeah. Yes.

Speaker B: Yeah. So I, I mean, I would love to. Like, again, this is a. A podcast about learning and making sure that entrepreneurs have some takeaways. So it's using the frameworks before you decide and also having some sort of foundation to make the decisions that you're talking about. Um, I'd also like to go back to what are some things that entrepreneurs don't know? They don't know some of the things that they should be thinking about that they haven't. That they likely don't.

Speaker A: Yes. So, and I actually just talked to somebody about this not that long ago. Even if you've worked in companies that were six figures, seven figures, eight figures, whatever it is, because your business is unique, as we keep saying, you getting to six figures is new, whether you've seen it before or not. So your journey to get there could be faster, slower, more, less, you know, and, and the one thing that we don't know, that we don't know is actually how long it's going to take for your business to get where you want it to go. Right. So we know a carrot, I think, takes 70 days to grow. And we know it's a carrot, but your idea, your fantastic team, your employees, credible services, your product, we don't know how long it takes.

Speaker B: Right.

Speaker A: And I think sometimes we get frustrated because we don't start from the place of I don't know, and it's okay not to know. And as you're not knowing, you're also putting those aligned steps in action, um, so that you give yourself the best chance, but it's just as new to you as everyone else around you. When you hit your goals and Miles Stones, I just don't think that we give that enough focus. Other things we don't know, that we don't know. I'm going to come at this from the lawyer lens. There's a very easy way to film, um, an LLC or a C corp or some of these things. And everybody, not everybody, most of the people I talk to who want to just start a business, they're like, well, I haven't formed an LLC yet. And my first response is good. It's a separate legal entity, and you have obligations on the legal side to that legal entity. Like, everything must remain violently separate. Your finances, nest, you know, all these things that you have to document, things. You're supposed to have board meetings with yourself. Those are the rules. I didn't make the rules but those are the rules. And if you just create the entity and you don't understand what goes in underneath it and something happens, for example, and you say, well, you know, thank goodness all my personal things are protected because I have this llc. And then they go digging in and they realize, well, no, no, no, you were running everything through your personal bank account or no, no, no, you were not paying your W2 employees. They were, you know, mischaracterized or whatever. Any of those things that could happen. The LLC doesn't, doesn't necessarily help you. So just from a legal standpoint, we make it so easy to start businesses, which I think is a beautiful, beautiful thing. I don't think, think that there should be a huge bar to entry. At the same time though, it is so easy to watch the media and to, and to watch, you know, the news and these well intending people who want you to succeed and they say, well, make sure you do this and make sure you do that. Um, and it's, it's from a place of, well, that's what we see everybody does. Or it's the place of, well, that's what successful businesses do. And I have Talked to enough CPAs and enough people in my life that say, actually you can hold off doing that until you have, you know, gross profits of X in this industry. And it's, it's interesting because I don't think we know that.

Speaker B: Yeah, yeah. I mean, especially things like becoming S Corp, right? That's the most, one of the most popular things on TikTok now everybody wants to do that. And I'm like, oh, slow down. It's not, not that easy. It's not that, um, not that beneficial depending on what you're trying to do. So I, I think being thoughtful, it's, I, what I hear today from this conversation, it's really about like being thoughtful and also then still taking initiative, being curious, being open and figuring out and taking the next right step. So there's, there's some sort of balance there, right?

Speaker A: Yeah, absolutely. And, and here's another thing. You know, the, the one thing I do highlight in the book as well is not every decision needs that, that level of, you know, dissection. And this is where I say, you know, for convoy coffee roasters, could we have gone faster? Probably. I, I fully admit I was terrified. I fully admit that we were getting into an industry food manufacturer, like who's, who's this chick, right? And she doesn't know anything. And so did I in some ways make decisions that held us back because of my own personal biases. Absolutely. Um, but you know, we make a million decisions, you know, every few days. I want to say the psychology that I read was we make like 30,000 decisions a day. When to take our foot off the gas and hit the brake when we're at a stoplight. Which hand do you brush your teeth with? Right. And you know, it's, it's so funny. I wrote an article that'll be coming out for Convoy Road Coffee Roasters that talks about how Hollywood uses coffee to tell story without having to have dialogue. Like, for example, you open a scene of a, uh, murder and you know, they pan across, you see a half eaten breakfast and there's, you know, he touches the mug and he says, this is cold. He doesn't say, this happened a long time ago. He says, the coffee's cold. And we read that as, oh, this must happen a long time ago. I've never seen anybody open up a scene and they pan in and they go, oh, that Diet Coke is flat. Yeah, we don't do that. We have a relationship to coffee. So when we start to become aware of the number of things that we automatedly read signals for don't require a lot of input, then we really can be sure that we're putting our diagnostic efforts in the things that truly matter. And you know, there were times where people were like, okay, you're, you're, you're not only, not only is the horse dead and not only are you beating the horse dead, you have analyzed this six ways from Sunday and now you're really actually hurting your business. And I, I had to come to terms with that and I did have to do extra, ah, what I would call extra mindset work um, because of my own lived experience. And not everybody needs to do that, but yeah, that self awareness to your point, that understanding where you are the balance and then what truly needs your cognitive focused, you know, decision making versus, hey, we've built it up long enough. I'm sure there's tons of things in your own business that just kind of run and it's kind of boring and you know, you don't have to do much with it. And that is the most beautiful place to be to make the next decision is everything is generally 85% of the time like just kind of being boring. But again, as entrepreneurs, man, we love those shiny pennies. We want to go and chase the next shiny object. And sometimes we do that without understanding all the implications of, you know, disrupting this beautifully running engine that doesn't need A lot of. A lot of attention.

Speaker B: So you have to learn how to prioritize, learn what is important and what is not and not. Not waste your time on those shiny pennies.

Speaker A: Um, it's.

Speaker B: It's such an interesting life to be an entrepreneur and to have to deal with all these things and think about all these things. So I'm happy that we have you to help us use a framework, um, to decide, because that's really important. Uh, we are at time, so I love this conversation. I love the conversation we had before. Um, we will definitely link to the book and make sure that everybody knows what things they need to think about before they decide. I'm curious, now that we've been talking for 40 minutes or so, um, uh, what are you going to be thinking about out of the conversation? What is going to be your takeaway?

Speaker A: My biggest takeaway, and I think what you brought back into my own sort of consciousness with this conversation is it's about, like, the startup and the starting and we're. Because I think once you walk past a certain point, you have. You've sort of earned speed. Right. And intuitive things. And your question, what about a startup? I was like, wow, you know, I don't really train them so much anymore. Not because they're not wonderful and worthy. It's most of the time the popular. Starting a business has become easy or just follow these steps or whatever. And I sometimes feel like trying to talk to them too early feels maybe a little overwhelming. And I never want to overwhelm a new business, um, because again, I might be scaring them the way I scared myself. Right. But I think, um, having the conversation earlier rather than later is something I need to be thinking about now. Because to your, to your point, the conventional wisdom only goes so far. I think it's okay being the disruptor.

Speaker B: It's okay being this disruptor. It's okay doing things differently. It's okay knowing who you are and, and taking what you like and leave the rest. So I think that's. That's right. Thank you, Don, for coming on and sharing your knowledge. Uh, it's always a pleasure to talk with you and I hope to talk with you again soon.

Speaker A: Absolutely. And Brian, thank you for hosting this conversation. It was wonderful.

Speaker B: Of course. Thank you for listening to the Mission Driven Business podcast. I'm your host, Brian Thompson. If you enjoyed today's episode, make sure to subscribe on Spotify, Apple, or wherever you get your podcast. And if you know another entrepreneur who could benefit from this conversation, please share it with them. Until next time. Keep building a business that creates both profit and purpose.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • Risk Management: Identifying and Insuring Key Employees Ft. Mark GageExitReadiness®️ PODCAST · on Key person insurance71 / 100
  • Vets Run My Multi-Million Dollar Business (Model Revealed)Angels, Exits, & Acquisitions · on Key person insurance55 / 100

More from Mission Driven Business

All episodes →
  • Why Better Systems Won't Fix Entrepreneurial Burnout43 / 100
  • Five Questions To Ask About the Future of Your Business
  • What I Believed About Business in 2016 and What I Know Now
  • A Decade in Business: Lessons, Gratitude, and What Comes Next
  • How to Review Your Business Finances Mid-Year
Explore the best B2B Leadership podcasts →
All Mission Driven Business episodes →