Lessons - When Survival Creates Success | Ariana Pareja - 3x Serial Entrepreneur

Summary

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Success Story with Scott D. Clary

Lessons – When Survival Creates Success | Ariana Pareja – 3x Serial Entrepreneur

Date: February 2, 2026
Guest: Ariana Pareja, Serial Entrepreneur

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Episode Overview

In this episode of the Success Story Podcast, Scott D. Clary explores the nuanced reality of building, scaling, and exiting businesses with serial entrepreneur Ariana Pareja. Together, they unpack hard-earned lessons about why founders sell, realities of venture capital, the importance of understanding your motivation, and how funding and exit strategies shape an entrepreneur’s journey. Ariana provides candid advice, grounded in her own successes and struggles, about key decisions founders face and how survival instincts can create paths to both freedom and fulfillment.

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Key Topics & Insights

1. Motivations and Mindset Behind Selling Your Business

[01:00]–[02:57]

• Define the "Why":
  Ariana stresses the fundamental importance of understanding why you want to exit your business.

  • Ariana:

    “You really have to ask yourself three major questions. And the first one is: why? Why are you really selling your company? Is it because you're burnt out? Is it because you're bleeding money? Is it because your co-founder is pushing you out?... Figure out the why.” (01:00)

• Avoiding Regret:
  Many entrepreneurs regret leaving a business simply because of burnout and boredom after the event, rather than a true strategic reason.

  • Ariana:

    "...you don’t know what you're going to do after. In that moment you're so burnt out that you just are like, I just want to sell it. But if you have a good operating business and it is cash flowing and you're burnt out, that's not a good reason to sell your business... Take a break." (01:48)

2. Prepping for an Exit and Dealing with Buyers

[02:58]–[03:43]

• Choosing the "Who":
  Identifying the right buyer is critical. Often, it’s a competitor, and dealing with the ego around that can be challenging.

  • Ariana:

    “You need to always think about if you are going to exit... what makes the most sense strategically... With service based businesses, they'll get purchased by a competitor. That's hard for an entrepreneur because the last 10 years they've been at war with this person.” (02:58)

• Working with Investment Bankers:
  Building relationships with investment bankers before considering an exit can be pivotal for tech startups aiming for a profitable sale.

  • Ariana:

    “...start to build a relationship with an investment banker way before you even start to think to sell. So that when you get to that process, they have your best interest.” (03:43)

3. Should You Build to Sell? The Fundraising Mindset

[03:45]–[05:45]

• Conflicting Advice in Entrepreneurship:
  Many entrepreneurs struggle with conflicting advice—should you build your business to sell, or focus on growth, or bootstrapping?

  • Host:

    “There's so much conflicting advice... and it's up to the entrepreneur to sort of figure out who's right when and who's right for them.” (04:43)

• Raising Money: OPM vs. Bootstrapping:
  Whether to use other people’s money (OPM) or bootstrap depends on the type and scale of the business.

  • Ariana:

    “If you're going after consumers, you need to raise money... you’re not going to be able to bootstrap that. ...In our case, we couldn’t... our competitors were publicly traded companies... The only thing that set us apart was speed.” (05:45)

4. Lessons from Raising Capital

[10:15]–[15:39]

• When You Take Money, It’s Not Just Your Company:
  Once you accept outside capital, ownership and control fundamentally shift.

  • Ariana:

    “Once you take on other people's money, it’s no longer your company. It's everyone's company now. You don't get to act like a dictator anymore; it's a democracy.” (10:49)

• The Danger of High Valuations and VC Milestones:
  High valuations can trap founders; VCs may set unrealistic milestones, leading to unfavorable follow-up terms.

  • Ariana:

    “A lot of times VCs... will give you this ridiculously high valuation... and milestones... They know that you probably won't hit those milestones. And so now it becomes this dependency they've built...” (10:49)

• Prioritizing Angel Investors Over VCs:
  Ariana advocates for angel investment as a preferable alternative, especially for those new to raising capital.

  • Ariana:

    “If you have to raise capital, angel investors are the way to go. ...VCs have so many people in their portfolio company... unless you're that one unicorn, they're not going to pay attention to you or care to help you.” (10:49)

• The Real Stress of Fundraising:
  Fundraising is all-consuming and may not yield the happiness or autonomy founders expect.

  • Ariana:

    “The entrepreneurs that I know that are the happiest have never taken on money because they have all their equity and they don’t have the stress and they didn’t feel like an employee in their own company that they built.” (15:30)

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Notable Quotes & Memorable Moments

• “If you have a good operating business and it is cash flowing and you're burnt out, that's not a good reason to sell your business. That's a good reason to take a break.”
  — Ariana Pareja (01:48)

• “Once you take on other people's money, it’s no longer your company. It's everyone's company now.”
  — Ariana Pareja (10:49)

• “Angel investors—the way to go. Definitely angel investors.”
  — Ariana Pareja (12:34)

• “The entrepreneurs that I know that are the happiest have never taken on money because they have all their equity and they don’t have the stress and they didn’t feel like an employee in their own company that they built.”
  — Ariana Pareja (15:33)

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Useful Timestamps for Key Segments

• Why Founders Really Sell & Avoiding Regret: [01:00]–[01:48]
• Choosing the Right Buyer & Dealing with Competitors: [02:58]–[03:43]
• Should You Build to Sell? Advice on Fundraising: [03:45]–[05:45]
• Hard Lessons from Venture Capital: [10:49]–[13:34]
• Prioritizing Autonomy and Mental Health: [15:30]–[15:39]

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Summary Takeaways

• Clarity of purpose: Know exactly why you want to exit—don’t let burnout dictate major decisions.
• Plan your exit: Build key relationships (like with investment bankers) early, and understand who makes the most strategic sense as a buyer.
• Careful with capital: Recognize that outside funding, especially from VCs, can compromise your control, autonomy, and future stress levels.
• Industry and context matter: Tailor your fundraising and exit strategy to your market, competition, and personal goals—not generic startup advice.
• Happiness isn't always growth: Sometimes, the best outcome is maintaining control and equity—even if it means slower or more deliberate growth.

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For the full episode and more lessons from entrepreneurs, visit Success Story Podcast.

Transcript

[Host]

In this Lessons episode, explore the mindset behind building, scaling and exiting a business without sacrificing control or fulfillment. Discover how to evaluate the real reasons for selling, understand how funding choices shape ownership and exit outcomes, and uncover the hidden trade offs of venture capital that redefine entrepreneurial freedom.

[Interviewer]

Like the last thing that you sort of spoke about is is exiting your last business. And I think that's a and we can talk about like the growth and all the different things that you sort of teach over to people now. But I mean that was the most relevant point in your life that you've dealt with more or less recently. So let's talk about your own personal journey in like growing, scaling, exiting a business. What are just some thoughts on how to prep your business for an exit? What are the things you should think about when you're exiting? Are you even happy with how you've gone through your various exits? Are the things that you would like do differently if you if you had the chance with any of the business you sold?

[Guest Entrepreneur]

Yeah, I think when it comes to selling your business, you really have to ask yourself three major questions. And the first one is why? Why are you really selling your company? Is it because you're burnt out? Is it because you're bleeding money? Is it because your co founder is pushing you out? Is it because your investor wants you out? Is it because your biggest customer is basically saying, I'm tired of paying this invoice every month, you're too expensive, I just want to buy you and just own your tech, so figure out the why. And you I know you've interviewed a lot of entrepreneurs and I'm sure there have been entrepreneurs on this show that have said, you know, I regretted selling my company because now I'm bored and I don't know what to do with myself now after.

[Interviewer]

After the event. Yeah, for sure, after the event.

[Guest Entrepreneur]

Exactly. Because the reality of it is you don't know what you're going to do after. And in that moment you're so burnt out that you just are like, I just want to sell it. But if you have a good operating business and it is cash flowing and you're burnt out, that's not a good reason to sell your business. That's a good reason to take a break. That's a good reason to go, maybe, I don't know, vacation for five, six months, find someone to run the day to day of it, add it to your. Just think of it as your investment portfolio. Give them whoever you hire some equity and that's a good Reason. But the second thing that you want to think about is who. Right. Who are you selling your company to? You need to always think about if you are going to exit, like what is the most, what makes the most sense strategically. You know, a lot of people, especially with service based businesses, they'll get purchased by a competitor. Right. And, and that's hard for an entrepreneur because the last 10 years they've been at war with this person.

[Interviewer]

Yeah.

[Guest Entrepreneur]

But if they look at who makes sense to purchase them, it's probably going to be a competitor. And that's hard to deal with your ego, but could be. And then the other question of who is if you're going like for example, you have a tech startup and now you want to exit. Finding the right investment banker makes all the difference. Right. Because you want to go after and find out and start to build a relationship with an investment banker way before you even start to think to sell. So that when you get to that process, they have your best interest. I mean obviously they're always going to have your best interest. They're a professional. But you want to go after and find that investment banker that has sold companies like yours at a multiple that you want.

[Host]

Right.

[Interviewer]

That's smart.

[Guest Entrepreneur]

Now and then when.

[Interviewer]

Yes. And. Well, I was going to say one other point too because it's good advice but it's counterintuitive to what a lot of people teach entrepreneurs, which is when you're building something, build it to sell. Right. And then have some sort of strategy in mind so that it, if you're taking on money at any point, an investor understands where your vision for the company is. So does that advice change if you're taking on investor money?

[Guest Entrepreneur]

No, that, that. I mean, yes and no. Yes. I mean obviously if you're taking on investor money that, and you have a growth based business, your plan is to sell. You know, I'm, I'm of the mentality that I've done service based and growth based businesses, you know, small SMBs, it's, it's a different kind of exit but.

[Interviewer]

It plays into, it actually plays into your mindset about taking on money as well. So you're not even taking on money unless you are trying to transition into a growth based business where you're hitting monumental milestones. So that's the whole difference between everyone who there's, it's so confusing because there's so much conflicting advice.

[Guest Entrepreneur]

Yeah.

[Interviewer]

There's people, I mean you listen to like the sharks on Shark Tank, which are all very successful entrepreneurs in their own right. And I think Damon John is always about opm, like other people's money, other people's money. Never use your own money. So, so you hear that and then you're like shit, well I have to find other people's money because I don't want to burn my own money. And then there's another way to build the business. So I think it's hard because there's so much and entrepreneurship is already hard as hell already. And there's all these different conflicting ideas because you're right and he's right in different circumstances. And it's up to the entrepreneur to sort of figure out who's right when and who's right for the them. And that is the most confusing thing. So if, if you were going to, if I was an entrepreneur and I was looking at all these different pieces of advice and you know Damon John on Shar tank saying use OPM and then you're saying actually build an MVP and then take on money if you have to grow, but don't take on money. How does that entrepreneur understand what, what they need to do? Like what it, it, it what figure out their goals?

[Guest Entrepreneur]

It depends on, on, on their industry, depends on their business. Right. So for example, if you're going after consumers, you need to raise money because going after consumers is really, really hard, especially on like a national scale. You're not going to be able to bootstrap that. I mean you could, but it would be really, really hard. And then you know, if you're going up against publicly traded companies, for example, like in our, our case, we could not, we didn't have the luxury to bootstrap, remind like our competitors were publicly traded companies that were coming after us every single day saying that they're going to squander us. And so the only thing that set us apart was speed, was just pure speed. That was the only thing that could really set us apart at that time. And so we needed to raise capital so that we could hire the best of the best in the country and, and just deploy quicker and faster than everybody else.

[Interviewer]

And, and what did you learn that was the only business you ever raised for Correct. Outside of, outside of literally buying properties in the uk.

[Host]

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[Host]

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[Interviewer]

So what did you learn? Raising money.

[Guest Entrepreneur]

Oh, gosh.

[Interviewer]

That's the first thing that even, like, before we recorded, I was saying how we met was at a tech conference. And that's the thing that you mentioned to me because I was going through a raise myself, which I'm literally still going through. And that, like, it's a testament to how long some of this can take, because I was, what, like, almost here.

[Guest Entrepreneur]

And a. Yeah, that was at Emerge last year.

[Interviewer]

Yeah. So it's been, like, an ongoing thing in my life. But then you mentioned, like, don't take on money if you don't have to. So obviously that comes from stress trauma. Yeah, it does. 100%. So. So what happened? Or what? Or what would you do differently?

[Guest Entrepreneur]

Oh, gosh, don't take such a high valuation. The thing about VCs. Well, let me rephrase that. So the thing about taking capital, just in general, is that once you take on other people's money, it's no longer your company. It's everyone's company now. You don't get to act like a dictator anymore, and it's a democracy, and I'm just. Yeah. So taking on VC capital as well is really tricky, especially if you've never done it before, because you don't understand how things work yet. And a lot of times, not all VCs, but a lot of times VCs, what they'll do is they'll give you this ridiculously high valuation, and they'll give you X amount of Runway, and they'll give you these milestones, and they'll say, okay, well, if you hit these milestones by this time, then we'll fund you again, yada, yada, yada. But they know that you probably won't hit those milestones. And so now it becomes this dependency that they've built. Right. So you as the entrepreneur, you don't hit these milestones, and then you have this value. Then. Then they're like, oh, well, okay, we'll give you Money again. But we're going to take preferred shares. And by the way, we want all the board seats and we want this and we want that, and they're in this position of power to negotiate whatever they want. And what are you going to do? What's your choice? You're either going to say, no, I'm not taking that term sheet and then your lights go out, then you go bankrupt, or you just say, okay, I guess this is what we're doing, and you just sign on the dotted line and you just move forward. So my suggestion would be, if you have to raise capital, angel investors, the way to go. Definitely angel investors. Because the thing about VCs, they have so many people in their portfolio company and unless you're that one unicorn, they're not going to pay attention to you and they're not going to care to help you. And, you know, a lot of times founders think that, oh, if I raise venture capital, the second I do it, I'll be replaced and they'll get into CEO and they'll get really involved. Actually, no, that's not the case at all. They don't really get involved at all. That's more growth in private equity. They get more involved. And so, you know, if you're going to be doing it all on your own anyways, you might as well just figure it out with some angel investors that will play friendly when it comes to raising again. And yeah, and not everyone's experiences that. But that was my.

[Host]

No.

[Interviewer]

But, yeah, you have to be, you have to be very careful because some, like venture capitalists are professional investors.

[Host]

Yeah.

[Interviewer]

And I think the one thing that I pulled out of front you just said is they'll, they'll play onto your emotions about a high valuation because you'll think, as an entrepreneur, I want to get a high valuation so I give up less of my company. Like, that's, that's the immediate entrepreneur mindset when it comes to raising money. But then that screws you in the future because if you think about how much money you actually have to make to make those investors happy.

[Guest Entrepreneur]

Exactly.

[Interviewer]

So especially at, I mean, if you look at the different rounds. Right. So I, these are all like, these are all guesstimates, but I think for like a, a seed, it's like they're looking for like 100x and then like a series A, maybe like a 30x and then like a series BCD, it could be like a 5x6x10x, whatever it is. But if you think about raising at, you know, if you want to make 100x on on $10 million like your company has to be like wildly successful.

[Guest Entrepreneur]

Yeah. You have to be.

[Interviewer]

Yeah.

[Guest Entrepreneur]

Very, very, very.

[Interviewer]

You have to be like very, very successful.

[Host]

Right.

[Interviewer]

So you have to be careful what you raise at and then there's. Then you have to do down rounds in the future and you have to.

[Guest Entrepreneur]

Have a huge total addressable market to really hit those numbers.

[Interviewer]

That's true. So know the tam. And then also if you think about it, if you are raising that much and then like that that second term sheet is not as favorable. Well, it's super time consuming to go raise money. So yeah, they're putting money right in front of you with shit terms. But like if you are a founder and you're raising more money from new people that you think are going to give you better terms, it's like a full time job.

[Guest Entrepreneur]

Oh it is.

[Interviewer]

And if you don't have money for an investment banker because you're trying to keep the lights on and pay salaries for another 3 months, you don't have the 10 or 15k retainer for the investment banker that can go help you with this at the same time. Right. So it just all around very stressful. I've never, I mean raising money has a place but the entrepreneurs that I know that are the happiest have never.

[Guest Entrepreneur]

Taken on money because they have all their equity.

[Interviewer]

Yeah. And they don't have the stress.

[Guest Entrepreneur]

And they don't have the stress and they didn't feel like an employee in their own company that they built.

[Host]

Thanks for tuning in. If you found this valuable, don't forget to hit that subscribe button so you never miss an episode. And if you want to dive deeper into this conversation, check out the links in the description to watch the full episode. See you in the next one. Sam.