One Big Idea 3 - Driving Enterprise Value: From Funding Architectures and Radical Letting Go to Systems-Driven Revenue

0:03Welcome to the Thoughtful Entrepreneur. You asked for it, so we made it happen. Every Friday, we're doing something a little different. Instead of one long conversation, we're packing in four of them, four experts, four big ideas, all in about the same time it takes to drink your morning coffee. We call it One Big Idea Friday, and the format is simple. I ask each guest one question, and they bring their single best question. idea for business leaders who want to grow without the noise. No fluff, no rambling, just the thing they actually want you to remember. I'm Josh Elledge. Let's get into it.

0:44With us right now with our next one big idea, Anthony Rose. Anthony, you are the founder and CEO of Seed Legals. You are found on the web at seedlegals.com. Anthony, thank you for joining us And thank you for sharing your one big idea. Let's hear it. All right. So hello. Thank you. Now, Seedlegals, it's a legal tech platform used by startups for fundraising. I talk to thousands of startups. I've seen everything. And my one big idea is the most popular way of startups to raise investment in the U.S. is with a safe. But safes are not safe. And let me explain. so once upon a time years ago when you wanted to raise investment it was called a funding round it was like a bus trip you'd get all the investors on the bus the bus could only leave when the last one arrives so you say you're raising five million dollars you have to find all these investors and when someone says i'd like to invest you go wait wait come back in three months when i've got everyone else but you really need the money now the problem with funding rounds is the legal fees are insane,$50 ,000,$100 ,000.

1:55So back in 2013, Y Combinator came up with an alternative called a safe, a simple agreement for future equity. I like to think of it, it's like getting an Uber instead of a bus trip. So as you find an investor, you say, can I send you the safe? So safes are nice and simple. It's like an IOU, it says, I'm going to give you money now, and you're going to give me shares later when you do a funding round later. And they've swept the industry. But, and here's my one big thing, safes are not safe. For an investor, if you're not familiar with it, there is something called QSBS, Qualified Small Business Stock.

2:36Qualified Small Business Stock means an investor, if they keep their stock for five years in a qualifying company, they pay no federal capital gains tax up to the higher of 15 million dollars or 10x their gain which is awesome and for founders you benefit from this as well but if the investor invests with a safe nobody's decided yet whether this five years starts from when they give you the money or when it converts maybe years later so for investors say for less good than getting stock and they don't have consent rights and other things. For founders, and here's the zinger, safes mean that your dilution stacks up against you if you use this YC post-money cap safe.

3:22It's super dangerous and founders don't realise you give 10 % here, you give 10 % there, then you do your first price round and you find you could be a minority shareholder in your own company because of the way dilution stacks up. So we think there has to be a better way. And we call it a safer. So safer. I love marketing names, is a simple mechanism that looks and feels like a safe. So it's familiar to investors, but it gives them their stock immediately. So they're getting their tax benefits clock starting immediately. And for a founder, the dilution doesn't stack up in the old way. So I think that once upon a time, well, in a few years' time, you're going to look back and say, you know what, for like 50 years, investors gave you money and you gave them stock.

4:13And then for like 10 years, you gave them a promissory note. But that's all over. We're now back to they give you money, you give them stock in a new, simpler, better, super inexpensive way. So that's the safer that we are now, the big idea on seed legals. I love that. Anthony, and so what would be, just one quick follow-up, you know, what types of startups is this, I don't know if this is an incredibly advantageous way of fundraising. Are there any kind of niches or specialties where you're like, no brainer? Okay, so basically every company that wants to raise equity investment is faced with this problem.

4:58So if you're an early stage company, like raising half a million, a million, a couple of million these days, you're probably raising the safes. Once you're raising three, five million plus, you're probably doing a funding round, often called a price round. So, however, what's been happening is that safes have been getting bigger and bigger. Once upon a time, they were like 20K, 50K checks. Now they're five million checks frequently. So the problem is getting bigger because everyone goes, we love the simplicity of the safe compared to the cost and time of the funding round. But my check size is getting bigger.

5:37We're getting into like, you know, high school territory, but we're playing with primary school instruments. So for any company, I'd say if you're raising, you know,$20 million or less, this is something that's of interest to you. Yeah. Anthony, your website is seedlegals.com quickly in about 30 seconds or so. Do you mind explaining what Seedlegals is? And to our friend that's listening, who should reach out and what should they do? All right. So once upon a time, if you were fundraising, you'd have to go to a law firm. Our platform changes that. So everything from getting investment ready, from incorporation, LLC to C-Corp conversion, raising with safes, doing a price round.

6:23It's a one-stop platform and the team that for a fraction of the cost of a law firm helps you get investment to grow your business. excellent and your website is seedlegals.com uh right on the front page there you'll see uh there's a start free button uh also talk to the team so uh anthony rose again you're the founder and ceo of seedlegals found on the web at seedlegals.com anthony thank you for sharing your one big idea thank you so much with us right now with our next one big idea latif hamilton latif you are the ceo and founder of spirit hoods found on the web at spirithoods.com and you are the you're actually a fractional cmo and the founder of growth operative and again the website for that is growth operative.com latif it's great to have you would absolutely love to hear your one big idea yeah it's a pleasure to be on.

7:26Thank you for having me. Yeah. So I, you know, I want to talk about why as entrepreneurs, we don't let go when we should, we don't let go of the hire that's maybe not the right fit. We don't let go of the product line. You know, there's so many things that we can struggle, even a company, maybe we need to shift and move away from the actual company that we have into something else. And I was reading this study and I found it to be really fascinating because it's essentially they had two groups and there was a group a was given a hundred dollar bill and they were told all you have to do to keep that hundred dollar bill is run a mile on a treadmill and group b was told we have this hundred dollar bill for you in order to get it you're going to have to run a mile on a treadmill so group a was given first group b was told they would get it after you know which group actually ran the mile the most it was group a and the reason for that is a couple there's a couple of reasons and and this gets into the psychology of of us as entrepreneurs right why we're why we're struggling to make some of the hard decisions that we know we need to make and um the endowment effect is is where we there's so there's two things there's endowment effect and loss aversion the endowment effect is where that group a was given that hundred dollars and once we once we're given something uh there's there's something that happens to us psychologically in which we feel like this is mine and now all the sudden becomes mind.

8:48Now, there's no difference in the fact that both groups had to run a mile to either keep or get that$100. But the reality is, is that once something's in your hand, it's in your possession, you will fight twice as hard to keep it, right? Regardless of the circumstances, that's just the nature of it. And the second thing is loss aversion. And this is also really fascinating, because we will actually experience, we believe that essentially, we experience about twice as much intensity or pain when we are losing something, aka letting something go, as we do the pleasure of gaining something, right?

9:21So that's a two-fold increase in intensity. So loss aversion is also at play. And we will struggle because we are afraid of that impending pain, that pain that may come from letting something go. Whether it's logical or not has nothing to do with it. And so So these are two main obstacles for entrepreneurs. And I just wanted to touch on them because I find them to be so fascinating. And I also, I've got a few tips and tricks on how we can overcome those challenges, right? How do we change or reframe the situation? And one way actually to simply reframe it is to actually, instead of looking at what you're losing, look at what you're gaining.

10:00What are you gaining by letting that employee go that's not the right fit? What are you gaining by letting that product line go that's taking up all that inventory space, where you can't get something else. So what are you gaining is a great way to shift and reframe that so you can counterbalance the fear and the uncertainty that you feel around letting go of something. Another thing is actually to calculate the cost of your inaction. So what is it on paper? What is it costing you to pay for that storage, right? What is it costing you? These things, those two alone will do wonders for you. And the last thing is, you know, really centered around, you know, what, what, oh, shoot, I forgot my last point here.

10:48If you want, we'll make an edit right here. And you just start with, and the last thing is. Okay, cool. Whenever you find it. Let me just read, like, what is my blank? Oh, yeah, starting fresh. Okay, so we can edit and do, and I'll just start from here. Let me do a quick countdown. We're going to leave a space of pause and then I'll do three, two, one, and then wait a second. And then, and the last thing is, okay, so here we go.

11:19and the last thing is starting fresh uh with a question the start fresh question sorry so essentially what you're just going to ask yourself okay if i was to launch this right now today that product line or what if i was going to hire that person would i do that would i do that and if the answer is no then you're being held hostage by the endowment effect and the loss aversion and that will help gauge how you can then let go of whatever it is that you need to go let go of it can help solidify your course of action to do the right thing to do the hard thing latif hamilton maybe i love it there's so many boy there's so many rabbit holes that i love to go down especially as someone who really loves uh you know critical thinking and getting curious about why am i thinking about this but you know i you know and i think about the number of especially those of us like working B2B and we might have a bad customer.

12:12Right. And it's like, Oh man, like he's causing a lot of stress on the team right now. But if we part ways, I'm going to lose that contract and ouch. Um, but you know, again, it's opportunity cost and, you know, and again, that's, it's a drag on everybody on your team culture. And that has a dollar, you know, that's expensive. It is expensive. It is expensive. Yeah. And especially when things are, you know, dodgy in the economy. You've got to make decisions. You've got to make them quick. Tell me about, you know, again, I mentioned spirithoods.com, which you've had a wonderful success as an e-com leader.

12:50What is the growth operative? Your website is growthoperative.com. Yeah. So, you know, we're a consultancy and we specialize in the e-commerce space, you know, so if you're, if you're business operating, selling a product or service, we started in fashion. My company, Spirithoods, which is still around today, more than 16 years, generated more than$60 million in revenue. And we take all of those concepts, everything I've learned there, and that same team also helps in consulting and building out other brands from SEO and GEO to operations to creative direction, marketing. I'm essentially a fractional marketing officer.

13:29Well, Latif Hamilton, again, growthoperative.com, spirithoods.com. Thank you so much for sharing your one big idea. Thank you for having me on.

13:45With our next one big idea, it is Dan Roshan. Dan, you are the founder of CPI Community. You're found on the web at nobrokemonths.com. You are the author of the book, Teach to Sell, Why Top Salespeople Never Sell and What They Do Instead. You've piqued my curiosity. And as well, you are the host of the podcast of the same name. So to our friend that's listening, you can go ahead and just search. And we've got a direct link to No Broke Months. Dan, your show. Well, Dan, it's great to have you. Let's hear your one big idea. Gosh, thank you. And you said CPI community. CPI stands for consistent and predictable income.

14:29And the way that we obtain that is through a methodology that I've developed called Teach to Sell. And Teach to Sell is built on one simple truth. People don't want to be – they don't want to be sold to. They want to be led. And most selling creates resistance because it feels like pressure, and it feels like you're almost begging, you're pushing. and the recipient of that is naturally going to resist. I mean, if you think about when you get a cold call, are you like, hey, how you doing? Or are you like, hey, I'm not available, click. Teach to Sell flips the script. Instead of asking, how do I close this person?

15:10It asks, how do I help this person to see more clearly? And that shifts everything. So the big idea is that Teach to Sell is a leadership method disguised as a sales method, where the salesperson's not the hero, the client's the hero. The salesperson becomes the guide who helps the client move from confused to clear, from stuck to moving, from doubtful to certain, and allows for you as a sales professional to be able to help and lead them so that they can think, so that they can get what they want. It positions so that the client is the one that is vital, not the sales professional. The sales professional is there to lead.

15:55And the goal is not to win an argument. The goal is to help the client to win their own decision-making process. Traditional sales often say, here's why you should buy. Teach to Sell says, let me help you to understand what's really happening, what it's costing you. What you want instead and what the path gives you to have the best chance to get there. It guides the client by teaching. And it understands what problem that the client is facing because that's a starting point. And then understanding why that problem matters now. And then what beliefs might be holding that prospect back from hiring you.

16:43When done well, the client never feels sold. They feel seen. They value you. They appreciate you. And the real antagonist of the concept of teach to sell is not the market. It's not the price. And it's not competition. And oh, by the way, it's even not the objections. the real antagonist, the deeper evil is not good enough. Whether that be, I'm not worthy, I'm not ready, I don't know enough, my website's not good enough, my knowledge isn't good enough, I may fail, or I just don't trust myself to decide. That is the demon. Teach to Sell helps people move through that inner resistance. It does not manipulate them.

17:32It helps them to understand themselves. And that is why it blends sales, influence, ethical influence, normal holistic programming, NLP, service, and leadership. And when you're able to guide somebody for them to be able to discover on their own the solution, they're going to choose that solution. So again, it positions you so that you can do three things, which I go through in the book, teach yourself, which are to connect energetically. That's called rapport, by the way. Then you ask a depth question, deep diving questions, to be able to discover the truth, the fear. What is it that's deep below the noise that's causing the other person to not take action?

18:21So the first step is to be able to connect with rapport. The second step is to ask a depth questions. And the third step is to be able to then actively listen to the energy. And that is what Teach to Sell is. Well, I love, Dan, your structure. That seems to me to be just a much easier way. For those of us who don't necessarily love the idea of selling because it feels like we have to convince somebody of something, that to me feels yucky. It makes me not real excited about coming to work. But I love working with people where I can help out and, you know, where it feels, you know, I love a sales conversation where it just feels so collaborative, where everybody's like, yes, this just, this works for both parties.

19:09It's a win-win. Everyone's grateful. I mean, that to me feels like the holy grail of a sales call. And it feels like your, the way that you taught that would encourage more of that kind of dynamic. It is. And it's vital to understand. I mean, you ask yourself, if you're a sales professional, ask yourself, do you want to be sold to? Does anybody here in my voice right now want somebody begging you for your business? And you already know the answer to that is no. So if the answer is that you don't want to be sold to, you don't want somebody, you know, spam calling you, you don't want all those spams in your emails, you don't want all those inappropriate outreaches, then what would cause us to believe that that's the way that we should approach sales and influence instead of guiding the other person through to their own solutions or to find their own solutions?

20:03Your book, Dan, is Teach to Sell, Why Top Salespeople Never Sell and What They Do Instead. Who should be reading the book and how do they get it? entrepreneurs, salespeople, and business owners who are tired of being stuck on that roller coaster, of waking up every single morning and not knowing where your next paycheck may come from. This book, Teach a Cell, it is a blueprint of four pillars that are believe in yourself, know how to find business, know how to scale an organization, and then know how to lead your company. This is a step-by-step guide on how you can do it with the philosophy of Teach to Sell.

20:47People listening right now, you can go to www.teachtosellbook.com. That's teachtosellbook.com. When you visit that site, I'll give you$10 ,000 of digital training. And if you want to just shortcut it, go to Barnes & Noble, go to Amazon, go to any of your retail organizations. The book is published on June 23rd, 2026, depending on when you're listening to this. It's either on the bookshelves right now, or you can go to teach to sell book.com to get the free$10 ,000 digital training to walk you through those four pillars. I love it. Dan Roshan, again, your new book, just hit the shelves, teach to sell why top salespeople never sell and what they do instead.

21:26Also your podcast of the same name, which we have all linked up as well. Dan has been a great conversation. Your website, teach to sell book.com and no broke months.com. Dan, thank you for sharing your one big idea. You're welcome.

21:45With us right now, Ronald Robinson, Ron, you are the founder of expanded learning Academy. You're found on the web at expanded learning academy.com. This is a great topic, Ron. It's great to have you please share with us your one big idea. Absolutely. Hey, thanks a lot, Josh, for having me on the show today. And you know, I like to start by saying thank you, everyone, everyone who's part of my development and my upbringing, because if it weren't for you, my social emotional learning competencies would be terrible. What is that? Let me tell you what social emotional learning is. The five core competencies that we see in education are self-awareness, self-management, social awareness, relationship skills and responsible decision making.

22:30Why are those things so important? Well, I've got to tell you, as a leader in my companies today, I utilize those things on a daily basis with intention, not just by accident. Let me tell you how that part started. I remember coming up in school and it was a terrible experience for me. I just wasn't supported the way that I felt like I could have been. Maybe because I had a super vivid imagination or I was just very curious about everything around me. Maybe I was just thinking about how I was going to save the world as opposed to listening to the lesson plan. Well, let me tell you, because of the social emotional learning, SEL core competency is supported by those who cared for me and loved me.

23:08They helped me through this process. Yes, I got Fs, Fs, Fs, Fs, Fs. Why am I getting, why am I failing all the time? Well, it wasn't until I was doing a keynote presentation when I discovered, huh, SEL was not complete. I laughed, I just laughed. Social emotional learning. I took all my F's and put it in the back end of that and decided that there were fundamentals missing. Social emotional learning fundamentals, meaning I need self-care. I need to be self-confident, self-assured, self-multiple things in order for my SEL, social emotional learning, to really take away. Now, how do we use this in business?

23:53Well, we have to first bring the best versions of ourselves so that way our teams and staff can see how it is modeled. What do we do? We deliver each of these core competencies with intention in each of our relationships with our teams. Well, again, it's going to look different for every group and for every organization. But what does not have to look different is you bringing the best version of yourself with understanding that your social emotional learning fundamentals start with you. And you as a leader, you have to lead by that example. Now, I can give a variety of ways on how I do it through my space in education, but that's irrelevant.

24:31It's really about how do we lean on each other? How do we support each other by modeling the things that are important to us? So my question to you is this, what is your SELF, S-E-L-F, social, emotional learning, fundamental competencies? How do those things render the intentions within and the outcomes within your organization. Listen, I'm not here to preach or to talk about that you should be doing things differently, that you should be the primary person and expecting people to deliver the things that you expect for them to deliver because you say so. That's not me at all. Really what it is is this.

25:11In order for someone to experience the best part of the day, which I would imagine you as a leader would want them to have, it's got to start with you, my friend. So take a look at yourself. and have an incredible rest of your day. I love it. You know, a lot, I think another way, Ron, that we could talk about what you're talking about are soft skills in the workplace. And, you know, you and I were talking about before we recorded, you know, soft skills are so critically valuable. And I would argue that a lot of positions get filled based on the competent, you know, potential employee or contractor who demonstrates incredible soft skills.

25:51Now, those soft skills are not always taught in school. They're not always modeled appropriately, you know, based on someone's upbringing. So, you know, we as leaders have a real opportunity here to, A, model, even though some of us, most of us, all of us need a little bit of work. I can speak for myself. You know, always, always, always working on that. But just how critical that is to teach soft skills along with the hard skills of the job. And I'm sure there's a lot of parallels there based on the work that you do. Yes, sir. Yes, sir. That is very true. Absolutely. And just so I understand, what is Expanded Learning Academy?

26:31Who do you serve and how might your work and mission be of interest to business leaders who are listening to our conversation? Absolutely. Yeah. And thank you for asking that question, Josh. So Expanded Learning Academy, what is where before during the after school program? And we provide supports not as a child care agency, but as an as an agency that supports the growth and development of children through using soft skills and blended through education and using academia as disguised learning opportunities. We service TK through 12, and eventually we'll be supporting at the collegiate level as we do partner with multiple colleges, especially the CSUs throughout the state of California.

27:16But primarily what we're looking at is bringing and introducing and encouraging incredible figures, adults, to come and be part of this process. How do we in turn ensure that students, when their parents pick them up, they ask them, how was your day, honey? Eh, what did you do? Eh, we just played. No, there's got to be something more than that. What our mission is to be the best part of the day. And that can only happen with incredible adults who first look at themselves through their social, emotional learning fundamentals. And we invite and encourage them to be a part of the process with us across the entire United States.

27:56Ron Robinson, you are the founder of Expanded Learning Academy. Your website is expandedlearningacademy.com. Ron, thank you so much for joining us. Sir, yes, sir. Thank you for having me. I appreciate you. With our next one big idea, it is Mark Osborne. Mark, you are the founder of Modern Revenue Strategies. You're found on the web at modernrevenuestrategies.com. And your book is, Are Your Leads Killing Your Business? How provocative. Mark Osborne, please share with us your one big idea. So if you're a business owner, you probably think all revenue is valuable and more revenue is better. But if your revenue actually breaks under scrutiny, it's not an asset.

28:43It's actually a liability. Businesses with less top line revenue, but better systems are actually worth more than businesses with lots of top-line revenue, but no systems. And the biggest problem is this scrutiny that I'm talking about shows up at the worst possible time, like a founder exit when you're trying to sell your business. When you're looking for an investment round or M &A activity, you're going to lose out on the multiple of your whole business, not just one year's worth of revenue. And a lot of this, you know, sort of systems that are lacking are you've built your business based on heroes.