In this episode of ThimbleberryU, we explore a fundamental question for professionals in tech: Which type of company is the right fit for your current stage in life and career? Whether it's a startup, a pre-IPO company, or a public corporation, each environment offers its own opportunities, challenges, and financial implications. Jag walks through the trade-offs with Amy Walls of Thimbleberry Financial, breaking down not only what to expect at each stage but also how to make a decision that aligns with our values, personality, and financial goals.
We begin by examining the startup world—fast-paced, creative, and filled with uncertainty. It’s a space for people who love to experiment and thrive in ambiguity. The upside can be big: ownership, impact, and equity at low initial prices. But the downsides—unpredictable income, fewer benefits, and emotional strain—are just as real. Amy shares stories of clients who initially thrived in startup life but found it incompatible with long-term needs like family time or structured days.
Next, we shift to pre-IPO companies, which often represent a middle ground. These firms offer more stability than startups but still retain a sense of mission and momentum. Equity typically comes in the form of RSUs, and while there’s real potential for financial gain, it hinges heavily on IPO timing—something employees can’t always control. Amy emphasizes the importance of planning for delays, setting aside cash, and staying flexible when managing that equity.
Public companies offer clarity and predictability—stable salaries, strong benefits, and slower but more structured growth paths. For professionals seeking balance, or with greater family or financial obligations, this environment often provides the support and stability they need. The culture tends to be more formal, but that predictability can actually empower people to do their best work.
Ultimately, the conversation centers around fit—not which company is best, but which is best for us, right now. Personality, financial goals, and life stage all play a role. A startup might make sense early in a career, while a more structured setting could become the right choice later on. Amy reminds us that romanticizing a company type—or even our own preferences—can lead us astray, and encourages getting honest feedback from those who know us best.
We wrap by reinforcing that job decisions should balance financial and emotional fit. Before accepting an offer, it’s critical to understand the equity structure, total compensation, pace of work, and company culture. Especially in today’s tight job market, doing our due diligence can prevent long-term regret and position us to thrive both professionally and personally.
00:00 - Intro and Episode Setup
00:49 - Startup Culture: Opportunity vs. Chaos
03:19 - Pre-IPO Companies: Growth with Guardrails
06:08 - Public Companies: Structure and Stability
09:27 - It's About Fit: Personality and Life Stage
11:43 - Culture, Pace, and Real-Life Trade-offs
13:43 - When the Job Market is Tight
14:17 - Takeaways: Equity, Compensation, and Culture
16:44 - How to Connect with Thimbleberry Financial
16:57 - Disclaimer and Wrap-Up
Jon Gay (00:10):
Welcome back to ThimbleberryU, I am Jon Jag Gay, joined as always by Amy Walls from Thimbleberry Financial.
Hello, Amy.
Amy Walls (00:16):
Hi Jag. It’s good to talk to you today.
Jon Gay (00:19):
And good to be on video for our full episode for the first time. So, getting over those nerves, but today, we're diving into a big career question for professionals in tech: What kind of company fits you best right now?
Whether we’re talking startup, a pre-IPO firm or a public company, each one offers opportunity and of course, trade-offs. Amy's here to help us unpack what makes each option unique and how to decide which one actually best fits your career and your life.
So, Amy, first off, the startups, what draws people to them, and what do they need to know going in?
Amy Walls (00:49):
Startups really attract people who love creating and problem-solving in real time. If you are someone who likes to see your fingerprints on a product and in the company from day one, the startup might be the right fit for you.
At a startup, you usually wear several hats, which can be really energizing if you like variety and ownership. The tradeoff though, is pace and predictability, if you will. Salaries also tend to be a bit lower with benefits leaner, and the stability less certain- and that's something we've definitely seen with clients.
These startups, they're high growth and high risk at the same time. And another thing to be aware of is that equity is typically offered as stock options with a really low stock price. The upside is that that can be financially meaningful, the downside is that it's never guaranteed [laughs], and so you can't count your chickens before they hatch.
The startup setting tends to fit people who get energy from experimentation, thrive in ambiguity, not the black and white thinkers, and can also handle financial risk. That's an important part of the startup, I believe. For other people, that same volatility can be very draining, kind of like introvert/extrovert just in a different way.
So, someone I know who we've worked with joined an early-stage startup and loved being creative, thrived in that creativity, but after a couple of years realized that they didn't have clear structure in their day, time for their family. And it wasn't that their choice to be with a startup was wrong, it just no longer fit their life or when they went in, it wasn't structured. They didn't have the boundaries to structure it so it could win for them long term.
Jon Gay (02:58):
It seems like more complicated than just left brain, right brain. There's a lot of trade-offs in a situation like this for sure.
Amy Walls (03:05):
Absolutely.
Jon Gay (03:07):
Alright, let's move on to the second category here, this is pre-IPO, we'll call it growth with guardrails. It's that middle ground between startup and a full-blown public company. What does that environment look like?
Amy Walls (03:19):
Pre-IPO companies usually have a proven product, they have solid funding, and a sense of momentum. They've survived those fragile years, really that early stage that we just talked about, but they haven't yet become fully corporate.
In this pre-IPO company, you tend to find more defined leadership and more defined roles, but still more of a sense of shared purpose and possibility than we might get when we talk about the public companies. Compensation is always a question. So, it often includes restricted stock units or a mix of RSUs and other options, and that creates opportunity for some meaningful upside, if you will.
The challenge with this pre-IPO company is usually timing. Meaning, the timing of an IPO, if that's the goal and if you're joining a pre-IPO company (it usually is), that can shift and you may not have any say depending on your role on what that looks like. You might be expecting that that's going to happen next year, and then it gets pushed out by two more years.
So, the challenge here is planning ahead for that uncertainty, and it can make a big difference especially when you think about where cash flow is coming from because that IPO provides stock. And while you have a promise of the stock before the IPO, the IPO is where you're actually going to get the stock which then equates to dollars, so that's important.
So, what we find is many people in the who like this space need to plan for the what if. And what I mean by that is planning for that IPO not happening when you think it will. So, it's setting aside cash ahead of time, just so you can kind of bridge that gap if it doesn't happen, and then have a more flexible plan for what to do with that equity when it comes up.
Jon Gay (05:34):
It sounds like this is going to be kind of the happy medium of our three situations.
Amy Walls (05:37):
Of course (laughs), yep. Yeah, Jag, it is the happy medium. The environment here is really geared towards people who want impact, but within a less risky situation than the pre-IPO, and a more solid framework all the way around, it's a balance.
Jon Gay (05:59):
Sure. And on the other side, you've got stability and clarity of public companies. What about the public company experience and what tends to draw people to that category?
Amy Walls (06:08):
Well, Jag, I think you just alluded to it, it is predictability (laughs). In many cases, stable salaries, established benefits, well-defined roles. Equity comes in and it has a more predictable schedule in the form of RSUs that will convert to stock and that can be sold once they vest. So, the value and the liquidity are really clear.
Benefits packages are often more robust. There's a 401(k) match in many cases, employee stock, purchase plans, parental leave, health and wellness programs, things that can really help people have a more fulfilling life.
Now, the tradeoff though is speed. Big organizations move slowly and are often driven by those quarterly goals. But for many people, especially those prioritizing family time or stability, that predictability actually feels more freeing. They feel they can do great work without constant reinvention.
Jon Gay (07:10):
Makes sense.
Amy Walls (07:11):
So, really, it's about where people thrive and some people thrive in this corporate culture in this structure, and it fits their entire career. Other times people might need a reset.
Jon Gay (07:25):
So, what it sounds like you're saying is the real question isn't which of these types of companies is best, but more like which company is best for me right now?
Amy Walls (07:33):
Jag, you get me (laughs), you so get me.
Jon Gay (07:37):
149 episodes, I hope so at this point.
Amy Walls (07:40):
(Laughs) Yeah. Fit here comes down to two things: who you are and where you are. You know who you are is wired for that creative chaos and independence. If you are, you're going to thrive more than likely in that early-stage environment. But if you're somebody who does best in a structured system with steady collaboration, really clear expectations and structure, then probably on the other end of the spectrum's better for you.
Where you are is about your life stage and the priorities that matter to you at this point. So, a startup might be really thrilling early in your career where expenses are really low, and you don't have others relying on you, but later on, it might feel really unstable, and obviously vice versa can happen. So, the key here to being happy and finding a place you can be longer term, and let's be honest, the tech space is not a space where people tend to stay long term.
It's important to understand your internal wiring, what makes you tick and your current season of life. Those two have to come together to tell you what fit might be best. And of course, then there's the variations between companies also.
I think sometimes, it can be exciting for people to say, “Ooh, I've been in this IPO space,” and this can be for any stage. It's got its benefits and they can really be talked up, and maybe even some prestige that goes along with some of that. But I'd say that for long-term financial success, it's about finding the place where you thrive.
Jon Gay (09:27):
So, before you say yes, before you put the ring on your finger, so to speak (laughs), before someone accepts an offer, what should they make sure that they understand?
Amy Walls (09:40):
Jag, that's a great question. A couple things are coming to mind, the first is equity. What kind of equity is the company offering? Is it stock options? Is it RSUs? When do they vest? How can you sell them? What's the holding period? Sometimes you won't have all those answers ahead of time.
There was a company that went public a few years ago and this happens, but I'm thinking very clearly of a few clients who worked for or worked for this company at the time. They went public and they expected all of the stock that had vested to be available while there was a restriction put on how much could be sold.
And it ended up taking quite some time for that initial equity to be able to be sold. And the company's stock price didn't stay as high as at initial launch. So, that was pretty difficult, I think (is) right word, for some of those employees and those clients.
So, outside of equity, compensation and benefits comes next to me. Really what's the full picture? Salary bonus potential, 401(k) matches, employee stock, purchase plan, out-of-pocket benefit costs. All of that factors into the overall financial picture.
And really, this episode's about happiness, finding a place you can be, but really why we're talking about this is because it's also important to have some financial or have stability in your job in terms of the income you need when you are needing income for your financially independence.
The next thing that comes to mind for me though, in terms of your question is culture and pace. There are those of us, and I've had times where working all hours of the day has been part of what I do.
Jon Gay (11:43):
That's you and I, as business owners for sure.
Amy Walls (11:45):
Exactly. And there are times that I've said, “Nope, at this point in my life, I am drawing some more clear boundaries and getting more time with my family and being there and being present is what's really important right now.” That's not to say that clients and work isn't important, it's just that at those times, I say I'm out of balance and something else needs me more, and I need to take care of that.
So, how much time do you have to put towards work? Are you happy working all hours of the day? How do people advance internally? How is the company going to support major life events? Those are all important questions.
Jon Gay (12:25):
That internal part is really interesting to me because I have a friend who... a coworker of hers likes to take a lot of trips, and in that particular culture at that company, there are some companies who really value personal time, and there are some companies who say, “Oh, well this person's not available,” and that might hurt them politically. So, knowing that political landscape I think is huge.
Amy Walls (12:44):
I think you're completely right, Jag. You made me think of one other thing: your ability to work virtually. So, when you talk about someone needing to be somewhere else, how much flexibility do you have in that?
So, really, I think what we're getting at is that that clarity upfront saves you from surprises later on, and really can help you align your decision with what truly matters to you, and that's the heart of what financial planning is.
Jon Gay (13:14):
I want to ask you for your takeaways, but before I do, I have one for you, and that is we're recording this on November 13th, 2025, the job market is not great, in a lot of sectors, and I think there's going to be that temptation to, “Oh, my gosh, I've got a job offer, I should take it.”
But I'm learning here with you, Amy, today, you really need to do your homework as far as what kind of company you're going to in terms of the financial structure, but also the corporate culture, and if it's not a good fit, maybe you don't take that first offer.
Amy Walls (13:43):
Exactly. It is tight and we hear that from our clients in tech right now almost daily with the stories of they'd like to find a new fit or they're not going to look right now because it's just too risky. And you're right, it is how do you balance what you are feeling pressure to have internally and financially, perhaps, with somewhere that you can stay knowing that this job market and this economy may not get better for a while.
Jon Gay (14:15):
Very fair. Any other key takeaways before we wrap up, Amy?
Amy Walls (14:17):
As we’ve talked about, and I think is clear to our listeners at least, I hope (if not, we need to know) – each company stage offers something valuable and something challenging. So, you have to pick your poison and your flowers.
[Laughter]
The right fit really depends on your personality, your priorities, and the season you're in. I'd also add here something we didn't touch on, is that it's easy for us as humans to romanticize things that we think we should have or should want, and to even do that about ourselves.
And so, finding that right fit and understanding your priorities and your season in doing that, it may be best to talk to others who know you well because they may have a very different assessment of your strengths and your priorities and where you'll be happy than what you do because of that romanticizing or other reasons. I know my family has put me in my place a couple of times on different things that I've thought about saying, “Oh no, this is sounding good to you, but this is not you.”
Jon Gay (15:36):
Longtime listeners of this podcast will not be surprised to hear my wife has done that for me many, many times (laughs).
Amy Walls (15:43):
Yep, exactly.
Jon Gay (15:45):
And vice versa, I'll say, and vice versa.
Amy Walls (15:46):
Yes. I think that's part of being a loved one.
Another takeaway, Jag, is planning ahead financially helps you focus on opportunity rather than uncertainty.
Jon Gay (15:58):
I like that.
Amy Walls (15:59):
So, each of these has opportunities. So, if you've got a couple offers and you have a financial advisor, I would expect that your financial advisor would be able to talk through this with you and what the pros and cons are.
Lastly, I think from this episode, it could be possible that our listeners are saying, “You're saying I should find the perfect company (laughs).” That's not the takeaway, the goal isn't to find that perfect company, it's to choose one that fits who you are and how you want or need to live now.
Jon Gay (16:31):
That is the perfect note to end on. I think the best decision is just about career growth. It's about creating alignment between your work and your life. Amy, if one of our listeners or viewers wants to reach out to you in the team at Thimbleberry Financial, how do they best find you?
Amy Walls (16:44):
Yeah, they can find us online at thimbleberryfinancial.com or give us a call at (503) 610-6510.
Jon Gay (16:53):
Great stuff. We'll talk again next year.
Amy Walls (16:56):
Sounds great, Jag.
[Music Playing]
Jon Gay (16:57):
Securities offered through registered representatives of Cambridge Investment Research, Inc. A broker dealer, member of FINRA, SIPC. Advisory services through Cambridge Investment Research Advisors, Inc, a registered investment advisor.
Cambridge and Thimbleberry Financial are not affiliated. Discussions in this show should not be construed as specific recommendations or investment advice, always consult with your investment professional before making important investment decisions.
Securities offered through registered representatives of Cambridge Investment Research Inc, a broker dealer, a member of FINRA, SIPC. Advisory services through Cambridge Investment Research Advisors, Inc, a registered investment advisor. Cambridge and Thimbleberry Financial are not affiliated.