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Hey, what is up?
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Welcome to this episode of the Wantrepreneur to Entrepreneur podcast.
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As always, I'm your host, Brian LoFermento, and I am so excited for today's episode because we don't have an amazing guest for you.
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We have two amazing guests for you that I am so excited to learn from both of them and hear their stories, because they are doing incredibly impactful and meaningful work, and I know that they're going to change the way that we view strategic planning.
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So let me introduce you to both of them.
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Their names are Adam Wolford and Sophia Shaw.
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They both have incredible backstories and they are both incredible not only people, but entrepreneurs and business leaders.
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I'm not going to toot their horns too much because they're going to give you their backstories, but I will say they're both incredibly accomplished.
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From their professional careers, They've both been on the boards of nonprofits, They've both led teams in for-profit industries and throughout different industries as well, at rapidly growing tech companies and companies in general, and together they have founded a company called PlanPerfect.
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Now we fell in love behind the scenes with what PlanPerfect is doing as soon as we read the headline on their website.
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Because Plan Perfect's website it states at the top success starts with a plan.
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Make it perfectly yours, and the way that they talk about their company is that it's technology inspired by nonprofit leaders, driven by tech experts.
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We are all in for a real treat today, because they are both incredibly accomplished.
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They're brilliant at what they do and we're going to learn a lot.
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That puts strategic planning into perspective.
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So I'm not going to say anything else.
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Let's dive straight into my interview with Adam Wolford and Sophia Shaw.
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All right, Adam and Sophia, it is so great to have you both on the show.
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First things first.
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Welcome to the show.
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Thank you so much.
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Heck, yes.
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So I'm excited for both of you to give us our backstories.
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Take us beyond the bio, Sophia.
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I'm going to kick it off to you before Adam jumps in.
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Who's Sophia?
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How'd you start doing all these cool things?
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I love the neon behind your intro about do what you love.
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I've done what I love my entire career and that's been in the arts, it's been in the environment and it's taken me to every which way of a non-profit, from being the person in the mailroom to the CEO, to the board chair, to consultant.
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I had the honor of leading the Chicago Botanic Garden for 10 years and teaching board governance of nonprofits at Kellogg at Northwestern.
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And then I met up with Adam and I'm doing what I love even more with PlanPerfect, our new software to help with strategic planning.
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I'm happy to jump in and give you a little bit more of my story.
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Sophia and I crossed paths a number of times in our career.
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I started my career in the consulting world, kind of following the big company thing.
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I went to Cornell undergrad, then went to Accenture, then Deloitte, never really actually doing what I loved, but doing what I thought I should be doing.
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When I went to get my MBA I really questioned that process and it was through Sophia's class that I kind of first interacted with nonprofits and fell in love with the space as well as entrepreneurship.
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So after I graduated from Kellogg, I went to run a product team at a series a startup, left that role two years ago and reached back out to Sophia.
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We started working together on some projects, realized how much we loved working together and wanted to make it something a little bit longer term, which led us to Plan Perfect almost a year ago.
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Yeah, it's a really exciting journey for us as well.
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Yeah, I love that Because for both of you, I think it's clear even in those brief overviews and backstories that entrepreneurial bug was always there, and so to see the two of you fully step into that Sophia, you talk about how important it is to do work that you love, and, adam, it sounds like you always knew and you were just kind of resisting along the way it's really cool how that's culminated in a business that's making a difference, obviously at the highest level.
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Where we have to start today is with regards to strategic planning.
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I have become a sucker for the strategy versus tactics ever since I started playing chess and started to understand the difference in chess terms between strategy and tactics.
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But I want to hear from both of you how do you define strategic planning and and I guess obviously with a real strong focus on that strategy element?
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every time you walk out of the door, you need to know where you're going.
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You need to have the overall strategy.
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Who do you want to be?
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Where do you want to go before you actually start taking your left and your right and stopping the stop sign?
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Those are all the tactical things that happen as you're right, and stopping at a stop sign those are all the tactical things that happen as you're getting from point A to point B.
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But strategy really is the big picture.
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How do you want to motivate change, make a difference in the world?
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And that's the big picture.
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But you can't get there without the roadmap.
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Yeah, I totally agree with what Sophia is saying.
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I think a lot of it for us is that the tactics are part of your broader your strategy.
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It's how you actually execute what you're trying to put forth into the world.
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But I think without having that overall roadmap of where you're heading, a lot of the times the tactics can feel aimless.
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So we really see this as a way of coordinating across your board members, your senior staff all the way down to your frontline employees, helping them to drive forward the overall vision and mission of the company through their strategic plan.
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Yeah, I want to go here with you both then, because I love that word roadmap, and so I think that entrepreneurship and nonprofit world, they're so tied together in the fact that we are mission driven, we know where we want to go, we have the destination in mind, but I would argue that this is a rare field.
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Nonprofit entrepreneurship we'll lump them all in together today, but it's a rare field where the roadmap is not paved for us.
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If I have a nine to five job, then fortunately I have somebody else who's telling me what they expect from me every single week.
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But when it comes to growing a business or growing a nonprofit and enacting those missions that we're all on, what is that roadmap?
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How do we even start to piece together that roadmap?
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Yeah, I'm happy to take this one.
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I think this was probably the hardest part of the transition to me was going from a more nine to five employee, or always having bosses, to really kind of driving on my own.
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And I think you know all of the adages that come in the world of entrepreneurship I think are so true, but some of them you have to live to really understand.
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So for me, I think the pivot or the hardest part of transitioning and figuring out that roadmap is just being willing to go do.
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I think as a consultant I was always planning for other people to go do things and a big part of my job was planning.
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I think what it's now pivoted towards and I think Sophie and I have done so well is really just executing quickly, moving quickly and then using those learnings to really inform our next steps or inform our roadmap.
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And I think you know the name of the podcast was so attractive to me because I felt like I was a wantrepreneur for so long.
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I was dabbling in different parts of it and I think really diving in headfirst was where I found so much of the value and the learning and defining that roadmap as you push forward.
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Yeah, sophia, anything you want to add there, because we're trying to make sense of how we're getting from point A to point B to that destination we want, but gosh, there's probably so many detours we could take and will take along the way.
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Yeah, we were talking recently about how a large part of strategic planning is really being able to communicate what you're trying to do.
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So it's not so much just saying to oneself this is what I want to do or saying this is my destination, but creating the messaging in a written down plan that you can share with your staff, your donors, anybody who supports you, the press, grant makers, because if you can't share a common language around your goals, then you're never going to get there, because you need everybody in an organization from the person who is on the front of the camera, like you, to all of the people who are helping you execute your vision and dream to be on the same page.
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Yeah, sophia, I want to keep going deeper there with you, just knowing that you've been the CEO of nonprofits before and you've obviously been at every different level of board engagements With that in mind.
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Obviously, people, that's what any business, any nonprofit, that's what life is about.
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I feel like we kind of distract ourselves when we call businesses B2B businesses, as if business to business is a thing and it's not just people behind each of those businesses.
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So, sophia, knowing that part of that roadmap is getting everyone on the same page, talk to us about some of those connections and really I'm picturing you as kind of the quarterback on the field of saying, hey, this is the way that we can all get together, because I would imagine that in many of the boardrooms that you've been in, if there's five different people, there's 50 different potential directions.
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How do you get everyone on that same page?
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That's really taking the ego out of it, and maybe that's why I've been drawn to non-profits my whole career.
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It's because, at the end of the day, it is more about the mission than it is about ourselves.
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Um, you know you're not.
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The only difference between a for profit and nonprofit really is is where the financial value is at the end of the day, because in a nonprofit, you don't have your, you don't have a shareholder.
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The that's the organization, is the is the main beneficiary, together with the people who's to whom you're making the impact.
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So I think the biggest issue, though, around any boardroom table is everybody's own personal stories getting in the way.
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Well, what do I want?
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How do I?
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How am I going to get something out of this?
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How am I going to get on the cover of Time Magazine?
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You know, is my legacy going to be maintained?
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So once we take ourselves out of it and we put really the focus on where we want to go and why we're there in the first place, things get a little bit easier.
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Yeah, I love that, Adam.
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I'm going to put you on the spot now to keep adding on to that, because obviously you come from an extensive for-profit background and so many of us obviously can relate to that in all different capacities of life, our professional careers and, of course, in business.
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With that in mind, there is that same degree of everyone moving in the same direction, towards a common goal.
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As Sophia said, that goal gets distributed in different ways, but ultimately we all want to achieve different things and removing ego is important.
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What are some of those things that the deeper you and Sophia go into Plan Perfect together, you realize, wait, we're focusing on the nonprofit world, but all these for-profit things that I gained along the years actually apply perfectly.
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Yeah, it's a great question.
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I think Sophia's point about removing the ego is likely why I've been so attracted to the nonprofit area recently and probably why I love working with Sophia.
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I think, even though she's been the CEO and was a professor, you can always feel like there's some deeper mission being driven rather than just sort of elevating herself.
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I think what's so interesting about the for-profit and non-profit space is that they're all accomplishing the same exact goal.
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I mean, a non-profit is a tax code, as Sophia always says.
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They're still trying to make money and execute on a mission.
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I think, of course, the non-profit mission is one that likely resonates with more people or probably feels a little bit deeper than some for-profit companies.
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But once you're under the hood, I argue that the businesses operate very similarly.
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I think there's also a really unique opportunity to bring the nonprofit space quote unquote up to speed with what's happening in the for-profit space.
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As you know, I think for-profit institutions are much quicker to adopt technology and move quickly with their strategy, fail quickly, make decisions and grow.
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In that way, I think what we're saying is that doesn't need to be reserved only for the for-profit industry.
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I think there's a ton of opportunity in the nonprofit space to leverage these same principles to continue to drive the nonprofit sector forward.
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And I think that's really what I've found is the most valuable part of my background is just seeing it live in the for-profit sector and being able to take the best components into Plan Perfect and, furthermore, into our clients and then the nonprofit sector as a whole.
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Yeah, I love the way you articulate that especially because you're obviously preaching to the choir here is that as entrepreneurs, we move fast, we break things.
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That's why there's that phrase of entrepreneurs jump off the cliff and build the parachute on the way down.
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For better and for worse, we're all willing to do that, and so you two are both obviously doing that in your own business as well with Plan Perfect.
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But what I really appreciate, adam, you talk about bringing that for-profit goodness to the nonprofit world.
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Obviously technology.
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It's one of those things that all of us entrepreneurs leverage.
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I would love for the two of you to introduce us to the technology behind your solution, because obviously that's a big part of it.
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Having that strategic plan is one thing, but I love the marriage between planning and technology.
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So what does that look like with what you're doing?
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Yeah, definitely.
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I think really where we started PlanPerfect was in sort of the mix of all of this generative AI movement or all of the building of AI that has happened in the past you know, three plus years.
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Of course, ai has been around for a lot longer than that, but I think it's become a lot more commoditized and accessible to founders like Sophia and I, whether you're non-technical or have a technical background.
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For us, I think, what we saw was this technology created a really unique opportunity to take what we were doing as a service all of the information that we had from Sophia's lengthy career, from my background and really turn it into a scalable technology leveraging a lot of this AI tooling.
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So we're quite fortunate that we've been able to have access to a lot of this proprietary data behind the scenes, which really helps our nonprofits actually develop meaningful strategic plans and use the technology not only to develop them but ultimately to execute them.
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I think the biggest thing that happens in the strategic planning world is that you get what everyone says is a plan on the shelf, and we've used the term as well.
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We really, since day one, have embedded in the technology the idea of not only creating great, amazing strategic plans, but also making sure that our users are executing upon them, so they can see the real benefit of having a strategic plan, which obviously is way more than just having the plan itself, but also then taking it and turning it into real tactical actions.
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Yeah, sophia, I'm going to kick it back to you because obviously we're talking about the speed of execution, the speed of technology.
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Adam's entered generative AI into the conversation, which these are all things that again us as entrepreneurs we soak that stuff up again, for better or for worse.
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The nonprofit world obviously has so many layers of complexity, of considerations.
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You've got the board, you've got the people who are actually executing the plans, the staff, the executive director.
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There's a lot of layers here.
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Fair assessment that nonprofits are moving a little bit slower and, if so, what's the tech adoption like when you guys walk in with plan perfect?
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The only reason that nonprofits are moving a little bit slower is that the majority of them have been founded by experts in their fields.
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So let's say you are a dentist and you've had a wonderful career as a dentist and you want to make sure that every person you cannot afford to go to the dentist gets adequate access to care.
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So then you begin a free clinic to make sure that everybody gets dentistry.
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Well, how are you supposed to know how to do all the business components?
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It's not a fair ask.
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So what we're trying to do is shore up the passions and the skills of all the people who have those specials, specialties to go out in the world.
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I think about it as a real democratization of it.
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Frankly, and in the past it was only the large nonprofits or large organizations let's forget about nonprofit or for-profits that could afford a consultant to make a plan, a business plan, a strategic plan or whatever you want to call it.
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And now, with these, this access to technology that we are harnessing in a software with a soft touch is really taking all the things that I wish I could give every day if I had an infinite number of minutes in the day that I could give from my heart and my skill set to every single person, that dentist, that, that, that doctor, that every teacher, every person who's ever wanted to make a difference in the world that through this software, we can now do that.
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Yeah, really well said and again showing your mission as well, something that we can all relate to in our own businesses.
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You brought up something there that I think we have to talk about, whether we're talking nonprofit world or small businesses, which is, of course, limited resources.
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Big businesses gosh, sounds like they can spend money on all these different things, hire consultants like Adam in his past life, but we don't all get to enjoy that on smaller scales.
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Talk to us about the limited resource nature, because I would imagine, in the talks that you both have with your nonprofit clients, is that technology is kind of one of those ways that we can enhance and better allocate our limited resources.
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What is the resource consideration look like when you're having these conversations?
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We've priced what we're doing at Plan Perfect to be affordable to most and, for those who may feel that it's a bit out of their reach, we're offering scholarships to the smallest startups.
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So it's our goal.
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Certainly, we're a for-profit startup we're not going to lie about that but we have such a passion for what we're doing that we want to make sure that everybody who wants access to a high-quality strategic planning tool can afford it and can get started on their journey with it.
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Yeah, and just to build off of that, I think the accessibility piece was always part of our mantra and thinking about the small to midsize nonprofits who maybe can't afford a traditional consulting engagement in order to build their strategic plan, they now have another outlet for developing their strategic plan.
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They now have another outlet for developing their strategic plan and, furthermore, we have partnered with consultants as a way of them increasing their capacity.
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So folks like Sophia who want to kind of grow their impact but maybe don't have a way of doing that by just you know, expanding their time, as great as that sounds, our tool is a really great opportunity to offload a lot of the administrative tasks that come with strategic planning while still being able to provide some of that personal touch.
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So I think it's always been about kind of having creating a more accessible approach to strategic planning than the traditional avenue of just having a consultant or a full service consultant take it on.
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And we're really excited about continuing to partner with the person side of this business as well to grow here.
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Yeah, I think that's why it's really fun to engage with both of you here today is because you're not only thinking about your clients, you're not only thinking about the nonprofit space, but, as fellow entrepreneurs just like the rest of us, you're also thinking about the execution, the implementation of it.
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You're not just building something great, you're building something great that people actually use.
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Talk to us about the implementation on the client side, because what I always joke with our internal team about is having a plan is great, but tying it to execution is the most important part of it.
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Talk to us about that side of the equation.
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Yeah, I think, like I said, it's always been a through line of ours.
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I think we've always been really passionate about making sure that what is in our system is also easy to execute against using our system.
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That's why we say we're an all-in-one solution and we're really hyper-focused on the strategic plan itself.
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So we have a light project management tool in the system, reporting tool that you know not, I don't want to say forces our customers, but incentivizes our customers to not only create the plans but also execute on them in the system, keep them updated, report that out to their board members, etc.
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And that's really where you see the value of a strategic plan right.
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In the end, if you just develop the plan and let it sit on the shelf, you're not actually going to extract the value from it.
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So I would say, through our user experience, we've also doubled down on making sure that our users not only create the plans but are also executing against it.
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Yeah, sophia, I'm going to put you on the spot with your former CEO.
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Hat on what's that execution side of the world look like?
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Well, it's not.
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It definitely is not.
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If you build it, they will come.
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You know, what's so interesting is that I actually haven't been an entrepreneur my whole life.
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I've never wanted to be an entrepreneur.
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I'm very, very happy in big organizations.
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I'm very happy coming to work every day, and I mean, I'm not lying that was a really hard thing.
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I mean having to make payroll for some points in the year 800 people was very stressful.
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So I'm not saying I'm adverse to stress, but definitely trying to make sure that the product meets the client's needs and that you reach more clients.
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It's really hard.
00:20:36.626 --> 00:20:38.380
It is definitely not.
00:20:38.380 --> 00:20:44.221
Oh, here's a great product, everybody's just going to come to you and buy it from you.
00:20:44.722 --> 00:20:58.808
So we've been using a lot of outreach to people we know in our industries, as well as some cold outreach to be able to share people with people, the power of the software.
00:20:58.808 --> 00:21:05.484
And then, once they get in it, there's that moment of moment of like oh, is it going to be as good as as you, as we hope it is, and it every time.
00:21:05.484 --> 00:21:06.767
So far it has been.
00:21:06.767 --> 00:21:27.191
Um, and I give a lot of credit to the, the 14 pilot users who came in with us at the beginning, um, they really gave us great feedback from which to grow, and even when they were um, maybe even they found a bug or something that they didn't love, they just gave us the feedback in such a meaningfully positive way.
00:21:27.191 --> 00:21:30.123
So we hope to continue to grow like that.
00:21:30.123 --> 00:21:30.964
There will be problems.
00:21:30.964 --> 00:21:37.404
There'll be problems with every single thing that anybody ever starts, but we'd like to interface with the client as much as possible.
00:21:38.315 --> 00:21:50.866
Yeah, I love those insights, especially because, when it comes to building solutions, which is what entrepreneurs do in different capacities, even if it's a service-based business, we're all bringing solutions to the marketplace and it's hard Sophie it's your point to understand.
00:21:50.866 --> 00:21:55.162
What are those features that people need right now, what are the nice-to-have features?
00:21:55.162 --> 00:22:08.067
And so we've all heard that concept of the MVP, the minimum viable product, but I'd love to hear because we are talking about strategic planning I'm totally going to put the two of you on the spot right now what's that roadmap look like for plan?
00:22:08.067 --> 00:22:13.611
Perfect, because when you're building something out, obviously so much of it is iterative, is about getting those pilot customers and that initial feedback.
00:22:13.611 --> 00:22:16.579
What's the roadmap look like looking towards the future?
00:22:17.643 --> 00:22:19.467
We were actually our first customer.
00:22:19.467 --> 00:22:42.184
We use the tool to build a strategic plan for ourselves, and the first iteration of it was like build MVP and then get two pilot users by end of year, and so I mean having a plan for us.
00:22:42.184 --> 00:22:44.088
This really makes us honest.
00:22:44.088 --> 00:22:49.821
We do have to use our own tool to keep our own plan, but I would say we look back at it.
00:22:49.821 --> 00:22:58.223
Actually, this morning we were talking about making sure that it was up to date and we're really pleased with how well we've done.
00:22:58.223 --> 00:22:59.428
Congratulations, partner.
00:23:00.196 --> 00:23:03.865
I mean in the small amount of time that we've been doing this.
00:23:03.865 --> 00:23:11.314
Um, so we're definitely, we're definitely, whatever it is, uh, walking the walk yeah, definitely.
00:23:11.335 --> 00:23:15.949
I think using your own product is huge and has been huge for sophie and I.
00:23:15.949 --> 00:23:29.136
I think also one thing we agreed upon early on was kind of getting the initial product out the door to users, even though it wasn't wasn't though it wasn't wasn't pretty or wasn't beautiful, and I think for us that was really around the plan creation piece of it all.
00:23:29.136 --> 00:23:37.665
Sophia always joked that it was a Divi bike, which is a very Chicago reference for anyone who's from Chicago listening, and I think now we've come a lot further than that.
00:23:37.665 --> 00:23:48.497
But for us it was really getting that early version out there to not only understand where it might have been broken from a bug perspective but, I think, also having customers in the fold thinking about their strategic planning.
00:23:48.497 --> 00:23:52.967
It became so natural to us to understand where this needed to expand.
00:23:53.146 --> 00:23:59.098
Next, it's really sitting closely with our customers and it's advice you'll hear in a million different ways from a million different people.
00:23:59.098 --> 00:24:13.000
I think for us it is definitely what is keeping us honest and keeping us building really impactful software is by sitting as close as possible to our customers, and our users I mean our first pilot users.
00:24:13.000 --> 00:24:18.141
We literally watched five hours of recordings of them using the system, so we were in it with them, right?
00:24:18.141 --> 00:24:27.648
And I think that's sort of a mantra that we've kept true at PlanPerfect and, from my perspective, we'll continue to stay true to for as long as we possibly can.
00:24:28.575 --> 00:24:35.267
Yes, I love those real life insights and it leads perfectly into something that I always love to ask co-founders when we have them here on the air.
00:24:35.267 --> 00:24:39.605
I love these duo episodes because I get to ask what's your executive time?
00:24:39.605 --> 00:24:40.435
Look like, sophia.
00:24:40.435 --> 00:24:49.086
You just revealed to all of our listeners that you both just looked at your strategic plan just this morning and, yes, kudos to you both for making things happen and taking action.
00:24:49.086 --> 00:24:50.701
But what does that look like?
00:24:50.701 --> 00:24:57.844
Is it a weekly meeting where the two of you sit down and you say, ok, let's look at where we are, let's look at where we want to be, let's look at progress, let's look at roadmaps?
00:24:57.844 --> 00:25:04.151
Is it a quarterly reflection where you both come to the better side of Florida, on the Gulf Coast, and you do something in person together.
00:25:04.151 --> 00:25:07.036
What's that?
00:25:07.056 --> 00:25:15.368
executive time look like We've had a nice mixture of getting together in person and then we spend a lot of time with a parallel play on Zoom.
00:25:15.368 --> 00:25:41.001
So that's just a term from being a mom and trying to just sit sometimes and go through all of our lists of things to do together on Zoom and not have to make every moment that we're meeting productive from a team point of view but productive also individually, like if you get into a meeting and just make a list of 400 things to do, then you leave and you feel sort of deflated.
00:25:41.001 --> 00:25:45.232
But we feel like we keep each other company a lot and then getting together in person is remarkable.
00:25:45.232 --> 00:25:48.403
We couldn't have done this without the opportunity to get together in person.
00:25:49.185 --> 00:25:55.308
Yeah, and I think the other, like deeper, layer here is the deep, deep level of trust that I have for Sophia.
00:25:55.308 --> 00:25:58.676
I think we don't need to necessarily be sitting side by side.
00:25:58.676 --> 00:26:03.222
I can totally trust that if she says she's going to do something, she'll do it at 100%.
00:26:03.222 --> 00:26:21.500
And I always joke with my partner that Sophia is my best friend, like we talk more than anyone else in my life now and we're always kind of shooting ideas back and forth and it's always been that way and I think it's because the product is so part of our combined passion and something we're so excited about that you know it does.
00:26:21.500 --> 00:26:32.626
The journey feels enjoyable, even when it's sitting and doing some of the less glamorous parts of being an entrepreneur, which has been a really powerful learning for me as I've built plan perfect.
00:26:33.414 --> 00:26:34.298
Yeah, I love that.
00:26:34.298 --> 00:26:34.981
Go ahead, Sophia.
00:26:36.016 --> 00:26:39.825
I mean, I have no idea how people build a company on their own.
00:26:39.825 --> 00:26:40.747
I just don't.
00:26:40.747 --> 00:26:50.067
I think that having this partnership and the partnership with you know, I never thought that in my mid-50s I'd become a tech entrepreneur.
00:26:50.067 --> 00:26:53.585
I mean that's ridiculous and I'm really proud of it.
00:26:53.585 --> 00:27:02.523
And probably Adam never thought in a million years that he'd find a business partner and somebody like me.
00:27:02.523 --> 00:27:16.060
So having two people at least who really trust each other, who've had now almost five years of at least knowing each other in different contexts, this is how the special stuff is made.
00:27:16.962 --> 00:27:28.679
Yeah, I love that, sophia, and yes, truth be told, entrepreneurship is a lonely journey, and my answer to your question of how people do it alone is they listen to podcasts like this one and they're joined by amazing co -founders like the two of you.
00:27:28.819 --> 00:27:31.405
So thank you for sharing those insights.
00:27:31.405 --> 00:27:40.286
Before we get to the last question that I ask in every episode, I want to squeeze one bonus in with both of you, because I love that neither of you are lifer entrepreneurs.
00:27:40.286 --> 00:27:42.391
You both, as you've said, said multiple times.
00:27:42.391 --> 00:27:54.162
It's kind of an unexpected transition for both of you, so I'm going to totally put you both on the spot and ask what's something that surprised you about the entrepreneurial journey that, once you started, plan perfect, you said whoa, holy cow.
00:27:54.162 --> 00:28:02.324
I knew that we were doing something cool and I knew it'd be a lot of work, but I didn't expect this the highs are really high.
00:28:02.765 --> 00:28:04.667
You know, it's like it's.