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Amid AI Noise, Bravo Focuses on Fundamentals
Business·Maria Soledad··11 min read

Amid AI Noise, Bravo Focuses on Fundamentals

Sees software ecosystem flourishing

Orlando Bravo’s initiation as an investor was the dot-com bubble burst of the early 2000s, which wiped out an estimated $5 trillion in stock market value. Sur­viving this trial by fire, to then go on to be­come the first Puerto Rican-born billionaire, has resulted in an optimistic but more tem­perate approach to the current Artificial In­telligence (AI) boom. 

Bravo is the co-founder and managing part­ner of Thoma Bravo, a private equity firm focusing on software companies, which cu­rrently manages $180 billion in assets. His investment philosophy often echoes the pre­cept established by Warren Buffet and by his mentor Carl Thoma. However, Bravo’s ap­proach to business is also marked by what he learned growing up at the tennis courts in Puerto Rico and Florida. 

“I found out pretty quickly that I wasn’t that good. But I did private equity, so that’s okay. I’ll take it. That’s really an important part of who I am, how I think about business, and how I lead,” Bravo said at a student talk at Stanford Graduate Business School, from which he has an MBA. 

“In tennis, when you get on the court with somebody, it doesn’t matter what your ran­king is, you could be ranked higher, you could be ranked lower, the other player might have more coaching, this or that, but you have to try to figure out how to win that match,” he said. 

So, tennis helped frame his approach to business deals. He competes for every deal, regardless of how much. Thoma Bravo has grown in the same way that you show up to every match, he argued to the Stanford students. 

Bravo’s business philosophy is more straightforward, saying that as an inves­tor, he looks past the flashy or trendy ele­ments of tech companies and looks for the fundamentals. This echoes the philosophy of Warren Buffet, the co-founder of inves­tment firm Berkshire Hathaway and one of the world’s leading investors for the past five decades. 

These fundamentals include looking for good quality companies that the market is currently undervaluing, healthy debt ratios, and businesses’ earning power over time, among other factors. 

We’ve Seen This Before

While the tech IPO (initial public offe­ring) landscape of 2021 was marked by an exuberance in valuations, Bravo reads the current AI landscape through the lens of a more distant, albeit impactful reference: the dot-com bubble. 

From 1995 to 2000, the valuation of emer­ging internet companies skyrocketed, des­pite most of them not being profitable or showing a path towards profitability. Bet­ween 2001 and 2002, the dot-com bubble burst and the result was that $5 trillion in market value was wiped out from the Nas­daq stock exchange. 

“The same thing that happened [then] is happening—the misunderstanding that oc­curred in the year 2000 when the dot-com bubble burst as we started investing in soft­ware companies. The first misunderstanding, just like now, is that these companies carry a lot of risk because they are technology companies and technology comes and goes,” Bravo said. 

The Thoma Bravo head had to learn this lesson the hard way during the dot-com bu­bble era. Forbes noted that at the start of his career— during the tail end of the dot-com bubble— he made disastrous investment choices. For example, his investments in NerveWire and Eclipse Networks resulted in $100 million in losses. 

“I learned I didn’t want to invest in risky things ever again,” Bravo told Forbes in 2019. “It was too painful to live through.” 

Bravo seems to understand that opportu­nity often comes from learning to pivot. He went to Stanford instead of Harvard Univer­sity, which was his top choice, because the former was the only university that gave him an enrollment deferment, allowing him to have an internship at Morgan Stanley. That put private equity in his path. Not getting a return offer from a summer job then led him to Carl Thoma, his former boss turned bu­siness partner. 

From his financial losses in the early 2000s, Bravo learned to lean into companies that

 have good fundamentals and offer speciali­zed services that engender a loyal clientele, he argued in his Forbes interview. 

What investors like Bravo are hearing and seeing today are similar narratives and bu­siness indicators to those at the beginning of the dot-com bubble. The business world is getting repeats about the transformative capabilities of these emerging companies, combined with business models that are not showing a path to profitability. 

“In the year 2000, almost all software com­panies also did not obtain profits, and we said that we could provide a model to take these companies from zero profits to marg­ins of 20%, 30%, or 40%. Because the gross margins of the companies were not very good. They were losing a lot of money,” Bra­vo said. 

He explained that the role of private equi­ty firms is to find the good companies from among the deluge of AI-related companies and provide them with leadership and a profitable business structure. The investor warned that part of the issue is that there’s probably not a big enough pool of business experts to take all these companies to the next level. 

Keep Your Feet on the Ground 

Major AI companies are attracting massive amounts of investment. In the most recent funding rounds for Anthropic and OpenAI, for example, they raised $30 billion and $40 billion, respectively. The AI sector also ranks first or second in economic growth, depen­ding on the analysis. 

Bravo sees a great opportunity to invest, particularly in software companies with po­tential whose value has dropped due to cu­rrent industry analysis. However, the Thoma Bravo managing partner is seeing two diver­gent strategies in AI investments. 

On the side of private equity firms, there is much greater resistance to investing in new companies because, aside from being a new technology, investors do not project that the­se companies will make money this year or in the short term. In addition, many AI compa­nies have an unproven business model. 

According to Bravo, the investment firms managing their exposure to AI intelligently are those making investments in promising LLMs (large language models) or AI infras­tructure companies, but at the same time “keeping their feet on the ground” regarding cash flow, business models, and the leader­ship at the helm of these companies. Large language models are “advanced deep lear­ning models trained on massive datasets— often billions or trillions of words—to un­derstand, process, and generate human-like language,” according to the website geeksfor­geeks.com. Examples include OpenAI’s GPT- 4 and Anthropic’s Claude 3. 

Venture capital firms, according to Bravo, are being very aggressive in investing in star­tups that have high valuations—sometimes without well-defined products—because no one wants to lose the opportunity to invest in the next “unicorn” like Google or Meta (the parent company of Facebook). The co-founder of Thoma Bravo used the acronym FOMO, popularized on social media, which stands for “fear of missing out.” 

“There is a hunger and FOMO is not going to end well… We believe AI is going to be trans­formative. It is definitely a transformative technology but with a business model that is unproven,” Bravo said. 

“The investments are astronomical, the bu­siness model is unknown, and most impor­tantly, there isn’t enough leadership in the world to develop these companies, period. You have to do sales and marketing, but the­re isn’t enough to create 100 companies wor­th $10 billion overnight.” 

Bravo also noted that AI companies that are at the bleeding edge of technology maintain a narrative of adoption at rapid speed, parti­cularly with the promise of the tasks that ge­nerative AI or LLMs can now take over from humans. From the more traditional corpora­te side, the Thoma Bravo head sees a more muted response that will take more years for AI adoption. 

Regardless of whether AI proponents are correct or those being more cautious are right, Bravo understands that both paths can lead to economic trouble. The loss of 50% of white-collar jobs, as some proponents pre­dict 

 destabilizing transformation for society. On the other hand, the problem with this boom is that AI companies do not yet have net pro­fits; if they do not start generating earnings in the short or medium term, it could have a negative domino effect on the economy. 

What Cannot be Copied 

While much of the public focus is on emer­ging AI companies, the value of many soft­ware companies that provide other services has suddenly dropped. In February, the S&P 500 index announced that this has been the worst quarter for software companies since 2002, when the dot-com bubble burst. 

For Bravo—again echoing Buffett’s inves­tment philosophy—this drop in valuations is an opportunity to invest in companies that have good fundamentals but where the market is misunderstanding what their role will be. 

One aspect that can protect software com­panies is the mastery of knowledge regar­ding how their respective industries function, which then translates to the needs of their industry and leads to the design of more spe­cialized products. This is knowledge that cannot be copied and one cannot give AI a prompt to replicate it. This falls in line with the concept of another Buffet concept— eco­nomic moat. 

The concept alludes to the moats dug around castles, which made it difficult for enemies to enter. In the economic sphere, the term refers to companies that have a competitive advantage that other busines­ses cannot replicate, which tends to secure their market share. 

Access Continues to be the Key Factor for Puerto Rico 

In technology and the emerging sector of artificial intelligence, Bravo recognizes that Puerto Rico is not in a competitive position regarding several aspects. 

To begin with, Puerto Rico does not have the established ecosystem that different re­gions of the United States have, such as the San Francisco Bay Area, which includes both Silicon Valley and the city of San Francisco. This area of California also has the benefit of its proximity to elite universities in scien­ce and technology like Stanford, the benefit of networks formed by having a high con­centration of these companies within a short distance, and the access to billions of dollars in capital that would be needed to compete with the largest AI companies. 

With the expansion of artificial intelligen­ce, the need to build data centers that house the computer servers LLMs need to function has also increased. According to a study by the real estate firm JLL, the demand for data centers is expected to grow by 23% each year until 2030; therefore, there is an emerging, though controversial, market in the cons­truction of these data centers. 

However, problems in Puerto Rico’s elec­trical infrastructure and high energy costs, in addition to the P.R. Electric Power Authority’s long-standing and as yet unre­solved bankruptcy case, make the Island an unsuitable destination for companies loo­king to build data centers. 

For Bravo, the card Puerto Rico can play is its relationship with the United States and how it can use this to compete with countries in Latin America. Puerto Rico can benefit by renting AI services to companies that offer services more specifically adapted for diffe­rent industries. 

“I believe Puerto Rico has many opportuni­ties because we have access, we can do bu­siness in the United States, and the United States can do business with us. We have a le­vel of protection and stability that perhaps is now in doubt in other parts of Latin Ame­rica,” Bravo said. 

“Being in a place of stability right now is su­per important for businesses and for coun­tries, and it seems to me that in Puerto Rico we are well-positioned for what is coming,” he added, who in a recent conference expres­sed support for Puerto Rico becoming a state. 

Editor’s Note: Not all Wins 

As this newspaper went to print, reports came out that Medallia, one of Thoma Bravo’s software companies, could not meet its $3 billion debt obligations. The company reportedly has yearly earnings of $200 mi­llion, which is not enough to pay interest on its debt. Thoma Bravo acquired software company Medallia for $6.4 billion during the aforementioned period of exuberant valua­tions of 2021. 

According to reports in the Wall Street Journal (WSJ) and Reuters, Thoma Bravo is negotiating with creditors the possibili­ty of handing over control of Medallia to its creditors, which are Blackstone, Apollo, KKR and Antares Capital. The WSJ reported that Apollo co-president John Zito criticized the arrogance of the private equity segment and used the Medallia situation as an example. 

For his part, during an interview with CNBC, Bravo declined to comment on Zito’s statement. While the Thoma Bravo head tried to present a positive outlook in gene­ral during the CNBC interview, Bravo ack­nowledged to the media outlet that the firm made a mistake in estimating Medallia’s rate growth that caused them to pay too much for the company.

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