EisnerAmper’s Alan Wink weighs in on separating hype from reality in AI investing, the impact on professional services, and why today’s innovators must be fluent in both capital markets and data.
By Kesav Dama
Artificial intelligence has quickly become the most consequential force in business and investment — disrupting entire industries while inflating the valuations of startups overnight. But are all AI companies truly innovating, or is this another bubble in the making?
In the final part of the wide-ranging conversation by Kesav Dama for The American Bazaar, Managing Director of Capital Markets at EisnerAmper Alan Wink explores the practical realities of AI’s impact on law, accounting, healthcare, and venture capital. He also shares sharp insights on pricing models, productivity gains, and how today’s founders — and their investors — can build for long-term success in a world of exponential change.
READ: Capital crunch, IPO backlogs, and the AI gold rush: What’s driving today’s market uncertainty (Part 1)
Inside the mind of an angel investor: Lessons from the frontlines of startup investing (Part 2)
Kesav Dama: What would you say to a young Alan Wink—someone who’s 20 or 21, just about to graduate college with a degree in accounting?
Alan Wink: Never stop learning. I say that now more than I would have 20 years ago, because the world is changing so dramatically. Especially in our business, we’re probably just in the first inning when it comes to technology transformation. AI has the potential to be a real game-changer—for better or worse—in accounting and tax work.
So, my advice to a young accountant would be to stay curious and stay current. Keep learning and keep your eyes on what’s happening in the business world. And honestly, it’s never been easier to stay informed than it is today. When I was younger, you’d read the Wall Street Journal and the New York Times every morning. Today, online access to news and tools makes it so much easier to stay up to date.
Kesav Dama: Across your advisory groups, do you see AI replacing a lot of employees? There’s a growing fear that AI could wipe out half the workforce.
Alan Wink: I don’t know about half, but AI is definitely going to have an impact. Think about all the repetitive tasks AI can now handle. We help our clients use technology to make their back offices more efficient, and yes, that often leads to headcount reduction.
Going back to your earlier question—what I’d tell a younger version of myself—I’d say one of the most important skills going forward is going to be data analytics. Not just compiling data, but actually turning it into actionable insights. That’s easier said than done, especially when people are overwhelmed by data today. Those with real expertise in analytics will be in very high demand.
So there’s no chance that, in the near future, a company can just say, “ChatGPT, advise me on how to improve operations,” right?
Look, we all use tools like ChatGPT and Copilot—I use them myself to help draft reports or memos. It saves you a few hours of spinning your wheels. But here’s the key: you have to be intelligent to use it effectively. You need to know how to ask the right questions. The better the question, the better the output.
So no, AI won’t be replacing advisory firms anytime soon, but it’s definitely going to change how we work—especially with things like tax returns and audits, which are more routine. AI will likely become part of those processes.
I’ve got to ask you something I’ve been running into more and more lately, especially on the angel investing side. As a startup advisor who’s “been there, done that,” you’ve probably seen this too: people who claim they’ve had two exits or were part of a successful team. And the first question that pops into my mind is—if that’s true, why do you need our money?
That’s a great question—and honestly, I ask the same thing myself. If someone’s had a successful exit, why are they raising outside capital?
I think the answer is that even with past success, many founders still recognize the value a venture capital investor brings to the table. Sure, all money is green, but not all money is the same. A VC helps keep a company on the right path. They can introduce strategic partners, help shape the business, and make sure the board functions as a true asset to the company.
That said, I tend to ask the question a bit differently. If you want to raise venture capital, I want to see that you’ve got some skin in the game—real cash invested. For someone who’s had one or two exits and made tens of millions, I’m not saying they should fully fund their new company, but I do expect some personal investment. It’s a signal of commitment.
What do you think is the right balance when it comes to investor involvement? One of the concerns I often hear from founders is, “If I bring in VCs, I’ll lose control of my company and get bogged down in corporate formalities.” What do you say to that?
First of all, I don’t think any VC wants to be a majority shareholder in a startup. The rationale is simple: if the founder and their team are left with only a minority stake, what’s their incentive to work 24/7? VCs understand that equity is the primary motivator for founders. That’s the real value—and you don’t want to give that up too early.
Of course, we all know that successful venture-backed companies typically go through several rounds of funding. By the end, the founding team might own only 20 or 30 percent of the company. But that’s after five or six rounds, and by then, the company has grown significantly. At that point, most founders would rather have a small piece of a large pie than a big piece of nothing.
I’ve always said that dilution can be a good thing—not in the context of a down round, but when you’re raising capital to hire great people, scale the business, and build real enterprise value. That kind of dilution is healthy.
That said, you don’t want to suffer heavy dilution too early, because then you risk working for someone else. It’s important to maintain control for as long as you can, especially in the early stages.
This isn’t directly related to startups, but I found it interesting that a couple of years ago, Bill Gates was no longer even among the top 20 shareholders of Microsoft. Apparently, his wealth manager advised him to diversify, and perhaps he didn’t anticipate how successful Satya Nadella would be. You’d think as a corporate insider, he would have seen Microsoft’s rise in cloud, the LinkedIn acquisition, and more. What do you make of that?
Most wealth advisors promote diversification, and I’m sure that if Microsoft disappeared tomorrow, Bill Gates would still be a very wealthy man. But yes, the optics can be interesting—people wonder, “Why is Bill Gates selling his stock?” Gates is probably just a tier below Warren Buffett in terms of influence, and when someone like Buffett sells a large position, it tends to rattle markets. People ask, “What does he know that we don’t?”
That said, even Buffett himself has a diversified portfolio—that’s how he became so wealthy.
That’s true, but Buffett also preaches concentration: focus on what you know and stick with it. So I was just fascinated to see Gates diversify out so much.
Sure, and remember what happened recently when Buffett started selling his Apple shares. It made headlines, and many smaller investors took that as a signal to reconsider their own holdings. If Warren Buffett’s selling, do I want to stay in?
It also raises the broader question: If you’re a founder and you sell your company but still retain shares, doesn’t that suggest a lack of trust in your successor if you offload too much? In Gates’ case, it almost looked like he didn’t have confidence in Nadella.
I’m not sure I agree with that. I don’t think you can read too much into it. Bill Gates did something amazing at Microsoft, and it’s equally impressive what the team that succeeded him has achieved. One of the biggest fears in public companies is always: What happens when leadership changes?
Take Apple, for example. When Steve Jobs passed away and Tim Cook took over, people questioned whether he could fill those shoes. Jobs was a visionary. But look at what Cook has done—he’s exceeded expectations, and the stock reflects that.
In tech, especially, companies are only as good as their next round of innovation. If they don’t keep innovating, they stagnate. That’s the pressure these companies are under—constant innovation and sustained growth.
That leads to another question. It’s not directly related to startups either, but there used to be this old-school thinking: stick to one business, focus deeply, and dominate it. But now we see companies like Amazon and Microsoft excelling in multiple industries. Elon Musk is involved in several as well. Are we seeing a return to the conglomerate model?
I don’t think we’re going back to the old-school conglomerate model, but the examples you mentioned—Amazon, Microsoft, Elon Musk—are outliers. These are led by extraordinary visionaries. Where most people see obstacles, they see opportunity. And importantly, they have the capital to take risks others can’t.
Take Amazon’s acquisition of Whole Foods. At the time, I remember thinking, “What are they doing?” But looking back, it’s clear they saw synergies most people wouldn’t have imagined. Beyond AWS, they also cracked the “last mile” logistics problem and are now pioneering drone delivery.
Jeff Bezos—and now Andrew Jassy—have built something remarkable.
There’s probably an Amazon package at my front door at least four or five times a week. And it amazes me how they can deliver that package to my home and at a cheaper price than I can buy it in a retail store. And that includes the transportation to get it to my front door. I can order it tonight and it’ll be there tomorrow morning. It is incredible. It’s incredible.
Shifting gears a bit—what exactly does your consulting group at EisnerAmper do? For younger professionals or startup founders who may not be familiar, what kinds of services do you offer?
We provide strategic advisory services across a wide range of areas for companies of all sizes. EisnerAmper represents 50 to 70 public companies, but most of our clients are middle-market firms across various industries. Personally, I spend a lot of time working with companies in tech and life sciences.
Over the past 35 years, I’ve worked closely with capital providers. Earlier in my career, most funding came from commercial banks. But in the tech world today, many companies are ‘unbankable’ by traditional standards. Instead, they rely on angels, venture capital, and other forms of professional capital. That’s where I focus much of my time—helping companies understand and navigate those capital markets.
Let’s say a company—XYZ Inc.—brings you in. What do you actually do? Do you look at operations, cash management, or treasury? How does the advisory process work?
We have advisory practices in many areas. There’s IT advisory, where we help clients improve efficiency through better technology use. There’s corporate finance advisory, where we assist with raising debt and equity capital. We also advise on mergers and acquisitions, divestitures, strategic alliances, and joint ventures.
But the most important thing is identifying the specific problem the client is facing. We don’t come in with a checklist to go through every corner of the business. Instead, we sit down with the ownership group, ask where they’re experiencing pain, and work to provide plausible, strategic solutions.