It was November 2021. After a big stimulus fueled rally, the markets had started to fall once investors realized that inflation was not really as transitory as the Fed claimed. Tech stocks and “science project” companies that went public through a SPAC, were especially hard hit.
Zillow (Z) had just decided to exit its ill-fated experiment with home flipping (iBuying as it is called) and the company’s valuation had dropped below that of Opendoor (OPEN). The irony of the situation was that Opendoor was primarily focused on the very same home flipping business that had gutted Zillow’s stock.
In this environment, I wrote a Seeking Alpha article with a rare sell rating on Opendoor and the stock went on to drop more than 97% from $19.73 in November 2021 to $0.51 earlier this year.
Since hitting bottom, the stock rebounded nearly ten fold to just over $5, fueled in large part by a meme stock rally. Leading the rally was Toronto-based fund manager Eric Jackson who in addition to his countless bullish posts on X, has also now decided to camp out outside Drake’s home, holding up a sign asking Drake to buy at least one share of Opendoor.
This is not a short report and I don’t have a position in Opendoor. The recent decision by Opendoor’s CEO to quit, prompted us to take a closer look at the company as part of our monthly C-suite Transitions article series.
Opendoor Technologies (OPEN): $4.7
Market Cap: $3.35B
EV: $4.71B
Key Insights
Company Profile
Opendoor Technologies is a digital real estate platform, often referred to as an “iBuyer,” that facilitates residential property transactions in the United States. Headquartered in Tempe, Arizona, and founded in 2014, the company enables homeowners to receive cash offers for their homes without using traditional listing channels. Through proprietary pricing models and virtual assessments, Opendoor purchases homes, conducts renovations, and resells them.
Opendoor’s fortunes are closely tied to housing cycles and mortgage rates. When interest rates surged and inflation climbed after 2021, Opendoor was hit especially hard, amplifying challenges already weighing on the broader tech sector.
On August 15, 2025, Opendoor announced that Carrie Wheeler had stepped down as Chief Executive Officer and as a member of the Board, effective immediately. Wheeler, who had served as CFO before taking over as CEO in December 2022, will remain an advisor to the Board through the end of 2025.
The leadership change follows mounting pressure from investors and company insiders, including co-founder Keith Rabois, who questioned whether a CEO with experience running a disruptive tech company might be a better fit. Activist investor Eric Jackson of EMJ Capital and crypto investor Anthony Pompliano also pushed for change, citing underperformance and strategic missteps tied to Opendoor’s pivot to an agent-led model.
In the interim, Opendoor appointed Chief Technology and Product Officer Shrisha Radhakrishna as President and interim leader while the Board searches for a permanent CEO. The succession process, according to the company, had been part of a broader “strategic evolution” initiated earlier in the year.
I applaud Ms. Wheeler for not participating on what appears to be a coordinated effort to pump up the stock. The situation reminds me of Bed, Bath & Beyond, which was a case study in my book about misguided capital allocation policies. A small excerpt from the book is given below:
“Bed, Bath & Beyond’s balance sheet, which had $1.4bn in cash and $1.5bn in debt in February 2020, was decimated by this misguided capital allocation policy and a string of losses that exceed over $1bn. By August 2022, the balance sheet was left with just $135m in cash compared to $1.7bn in debt.
The tragedy was not just limited to the company’s financial statements or the fact that it was now closing stores and laying off employees. Bed, Bath & Beyond’s CFO, Gustavo Arnal, plunged to his death from New York’s Tribeca skyscraper in what was ruled a suicide. Both Mr. Arnal and the company had been sued for participating in a pump and dump scheme during the meme stock rally of 2020 and 2021.
A combination of declining sales, losses, and a misguided capital allocation policy with buybacks at exactly the wrong time caused the company to let go of Mr. Tritton in June 2022. Less than three months later Mr. Arnal lost his life.”
Eric Jackson’s Big Bet on Opendoor
Eric Jackson, the Canadian hedge fund manager behind EMJ Capital, has reemerged as one of Opendoor’s most vocal supporters. Years ago, when the company was valued at $20 billion, Jackson was bullish on its prospects. Now, after a bruising downturn that required a reverse split for the company to maintain its Nasdaq listing, he is back with an even bolder call: Opendoor could be a “100-bagger”, with shares potentially climbing to $82 over the next few years.
Jackson’s declaration, posted on X in July 2025, sparked renewed interest in the stock.
Within a week, Opendoor’s shares surged nearly 200 percent, driven by retail investor enthusiasm. For a company that had been written off as another SPAC casualty, the reversal in sentiment was striking.
The Carvana Playbook
To bolster his argument, Jackson points to a prior turnaround he successfully championed: Carvana (CVNA). For Jackson, this is not unfamiliar territory. His career is marked by high-profile missteps and dramatic rebounds. His hedge fund endured a punishing 2022, with assets under management shrinking after his largest client withdrew capital. He was not as fortunate as Cliff Sosin of CAS Investment Partners, who rode Carvana down 99% from its peak and then right back up again to new highs.
The online auto retailer had lost 98% of its market value as bankruptcy fears swirled in 2022, but Jackson went on CNBC months before the stock bottomed and declared his conviction. Investors who followed him endured further losses but were ultimately rewarded with a staggering 1,000% gain in 2023. Carvana shares have since continued their upward trajectory, hitting an intraday high of over $400 on July 31, 2025, before giving back some of those gains.
Jackson now sees parallels with Opendoor. Where most investors see structural flaws, Jackson sees asymmetric upside, a possible repeat of Carvana’s so-called “epic comeback.”
Jackson’s thesis centers on three key points:
If interest rates decline, housing activity picks up, and Opendoor leverages artificial intelligence to sharpen pricing and inventory decisions, Jackson believes margins could expand toward 15 to 20%, transforming the company’s profitability profile.
That is a lot of “ifs” that have to all fall in place for his desired outcome.
Jackson concedes that Opendoor’s model is capital-intensive, dependent on pricing algorithms, and highly sensitive to housing cycles, some of the same risks Carvana faced. The concern isn’t necessarily about the innovation itself, but whether Opendoor can ever generate consistent profits.
Jackson has also begun acting as a quasi-activist. He has urged Opendoor to pursue a capital-light model, cut risk exposure, and focus on execution rather than flashy growth strategies. He has even floated the idea of bringing back co-founder Keith Rabois to stabilize leadership after Carrie Wheeler’s resignation.
For Jackson, Opendoor’s recovery will not come from quick fixes or meme-stock hype, but from disciplined execution and smarter use of technology. Still, his social-media presence and bold price targets have undeniably fueled a retail-driven rally, blurring the line between activism and cheerleading.
The Investor Lens
Jackson’s renewed conviction raises a critical question: Is this another Carvana-style asymmetric opportunity, or a value trap disguised as a turnaround? Housing demand remains cyclical, financing costs are high, and the iBuyer model is unproven at scale.
On the other hand, if he can engineer a sustained rally in the stock and the theory of reflexivity kicks in, the company could do a secondary offering or two. The new found capital could then be used to transform hype into reality and I have seen this playbook work very well for an unnamed EV company.
Financials
Revenue and Profitability: Opendoor generated $1.6 billion in Q2 2025 revenue, up 36% sequentially and 4% year-over-year, slightly above expectations. Adjusted EBITDA was $23 million, marking its first time achieving profitability in three years, though GAAP net loss remained $(29) million versus $(92) million in Q2 2024.
Adjusted net loss narrowed to $(9) million from $(31) million, and contribution profit reached $69 million with a margin of 4.4%, down from 6.3% in Q2 2024. Margins remain thin, reflecting high acquisition and renovation costs.
Balance Sheet & Liquidity: As of Q2 2025, Opendoor held approximately $789 million in cash and equivalents, down from its 2021 peak of $1.73 billion. Total liabilities were $2.28 billion, reflecting a modest decrease from quarters, while total assets were approximately $2.91 billion.
Net debt was nearly $1.39 billion. The company also maintains $7.8 billion in non-recourse, asset-backed borrowing capacity, with only $1.8 billion drawn.
Inventory management remains a key focus, with 4,538 homes valued at $1.5 billion, down from $2.2 billion in Q2 2024. The pace of acquisitions slowed sharply, reflecting a shift toward a capital-light, agent-assisted platform.
Second Quarter of 2025 Financial Results (Press Release) (Shareholder Letter)
While the quarter showed slight improvement, the near-term outlook is less forgiving.
Outlook
Q3 guidance points to $800–$875 million in revenue, a steep sequential drop of nearly 50%, with contribution profit of $22–$29 million and negative Adjusted EBITDA (–$28M to –$21M).
Macro Headwinds and Housing Market Impact
The broader housing market remains under pressure, with mortgage rates in the high 6% range and affordability near historic lows. Buyer demand is weak; only 12% of consumers believe it is a good time to buy, while sellers outnumber buyers at the widest margin in over a decade.
These dynamics have produced low clearance rates, high delistings, and the slowest spring selling season in 13 years, trends that are expected to continue through the second half of 2025. Given these conditions, Opendoor anticipates a steep sequential revenue decline in Q3 and Q4 2025 relative to Q2, along with further margin compression. Older, lower-margin homes in inventory are expected to weigh on contribution margins, making year-over-year improvement unlikely.
Conclusion
What we saw with Carvana was an extreme outlier event and a repeat of a similar outcome, while possible, is highly improbable. Given how these meme stock rallies tend to play out and what has happened with Carvana, it is nearly impossible to go against the tide. Investors relying on metrics grounded in reality will get swept out with the tide and suffer losses.
Sudden C-suite departures can be a red flag for investors, but in this case, I believe Ms. Wheeler made the right decision not to participate in this high-stakes casino game.
CEO
CFO
General Counsel/Chief Legal Officer
Others
Appointments
1. Dollar General (DG): $111.2
On August 19, 2025, the Board of Directors appointed Donny H. Lau as Chief Financial Officer, effective October 20, 2025.
| MarketCap: $24.47B | Avg. Daily Volume (30 days): 3,165,146 | Revenue (TTM): $41.13B |
| Net Income Margin (TTM): 2.81% | ROE (TTM): 15.53% | Net Debt: $16.17B |
| P/E: 21.22 | Forward P/E: 20.25 | EV/EBIDTA (TTM): 14.85 |
| P/S (TTM): 0.59 | P/B (TTM): 2.58 | 52 Week Range: $66.43 – $117.95 |
2. J.B. Hunt Transport Services (JBHT): $145.79
On August 18, 2025, the Board of Directors of J.B. Hunt Transport Services appointed A. Brad Delco to serve as Chief Financial Officer of the Company, effective September 1, 2025.
| MarketCap: $14.11B | Avg. Daily Volume (30 days): 1,045,498 | Revenue (TTM): $12.06B |
| Net Income Margin (TTM): 4.56% | ROE (TTM): 14.26% | Net Debt: $1.99B |
| P/E: 26.51 | Forward P/E: 23.93 | EV/EBIDTA (TTM): 10.09 |
| P/S (TTM): 1.17 | P/B (TTM): 3.90 | 52 Week Range: $122.79 – $200.40 |
3. Target (TGT): $97.96
On August 15, 2025, following a comprehensive succession planning process, the Board of Directors of Target Corporation appointed COO Michael J. Fiddelke as Target’s next Chief Executive Officer and a member of the Board, effective February 1, 2026.
| MarketCap: $44.51B | Avg. Daily Volume (30 days): 6,542,952 | Revenue (TTM): $105.64B |
| Net Income Margin (TTM): 3.72% | ROE (TTM): 26.40% | Net Debt: $16B |
| P/E: 11.42 | Forward P/E: 12.97 | EV/EBIDTA (TTM): 7.13 |
| P/S (TTM): 0.42 | P/B (TTM): 2.94 | 52 Week Range: $87.35 – $161.50 |
4. Crown Castle (CCI): $100.15
On August 4, 2025, Crown Castle announced the appointment of Christian H. Hillabrant to serve as the President and CEO, effective September 15, 2025.
| MarketCap: $43.61B | Avg. Daily Volume (30 days): 3,186,915 | Revenue (TTM): $6.47B |
| Net Income Margin (TTM): N/A | ROE (TTM): N/A | Net Debt: $29.47B |
| P/E: -11.13 | Forward P/E: 43.63 | EV/EBIDTA (TTM): 18.58 |
| P/S (TTM): 8.04 | P/B (TTM): -32.34 | 52 Week Range: $84.20 – $120.92 |
5. Procter & Gamble Company (PG): $156.96
On July 28, 2025, The Procter & Gamble Company announced that Shailesh Jejurikar, currently Chief Operating Officer, has been elected President and Chief Executive Officer, effective January 1, 2026.
| MarketCap: $367.66B | Avg. Daily Volume (30 days): 8,010,969 | Revenue (TTM): $84.28B |
| Net Income Margin (TTM): 18.95% | ROE (TTM): 31.24% | Net Debt: $26.97B |
| P/E: 24.15 | Forward P/E: 21.74 | EV/EBIDTA (TTM): 18.63 |
| P/S (TTM): 4.36 | P/B (TTM): 7.48 | 52 Week Range: $149.91 – $180.43 |
Departures
1. Waste Management (WM): 225.83
On August 21, 2025, Waste Management EVP and CFO Devina A. Rankin announced her resignation, effective November 1, 2025. She will serve as executive advisor through March 2026 to support the transition, as she shifts focus to education and non-profit service.
| MarketCap: $90.97B | Avg. Daily Volume (30 days): 1,650,003 | Revenue (TTM): $23.95B |
| Net Income Margin (TTM): 11.36% | ROE (TTM): 32.69% | Net Debt: $23.58B |
| P/E: 33.56 | Forward P/E: 28.22 | EV/EBIDTA (TTM): 16.56 |
| P/S (TTM): 3.80 | P/B (TTM): 10.01 | 52 Week Range: $199.69 – $242.58 |
2. J.B. Hunt Transport Services (JBHT): $145.79
On August 18, 2025, the Board of Directors of J.B. Hunt Transport Services announced that Chief Financial Officer John Kuhlow steps down but will continue to serve in an executive capacity as the Company’s Chief Accounting Officer effective September 1, 2025.
| MarketCap: $14.11B | Avg. Daily Volume (30 days): 1,045,498 | Revenue (TTM): $12.06B |
| Net Income Margin (TTM): 4.56% | ROE (TTM): 14.26% | Net Debt: $1.99B |
| P/E: 26.51 | Forward P/E: 23.93 | EV/EBIDTA (TTM): 10.09 |
| P/S (TTM): 1.17 | P/B (TTM): 3.90 | 52 Week Range: $122.79 – $200.40 |
3. Target (TGT): $97.96
On August 15, 2025, following a comprehensive succession planning process, the Board of Directors of Target Corporation announced Brian C. Cornell will step down from his position as Chief Executive Officer and will continue to serve as Chair of the Board in an Executive Chair capacity.
| MarketCap: $44.51B | Avg. Daily Volume (30 days): 6,542,952 | Revenue (TTM): $105.64B |
| Net Income Margin (TTM): 3.72% | ROE (TTM): 26.40% | Net Debt: $16B |
| P/E: 11.42 | Forward P/E: 12.97 | EV/EBIDTA (TTM): 7.13 |
| P/S (TTM): 0.42 | P/B (TTM): 2.94 | 52 Week Range: $87.35 – $161.50 |
4. Expand Energy (EXE): $95.30
On August 14, 2025, Expand Energy announced that Mohit Singh, Executive Vice President and Chief Financial Officer of Expand Energy, will depart the company to pursue other interests due to a termination without cause, effective August 13, 2025.
| MarketCap: $22.63B | Avg. Daily Volume (30 days): 3,330,557 | Revenue (TTM): $8.86B |
| Net Income Margin (TTM): 2.32% | ROE (TTM): 1.46% | Net Debt: $4.46B |
| P/E: N/A | Forward P/E: 10.04 | EV/EBIDTA (TTM): 9.07 |
| P/S (TTM): 2.59 | P/B (TTM): 1.55 | 52 Week Range: $69.12 – $123.35 |
5. Incyte (INCY): $84.84
On August 4, 2025, Christiana Stamoulis, Chief Financial Officer of Incyte Corporation, notified the company of her intent to step down from her role to pursue another opportunity, effective September 16, 2025.
| MarketCap: $16.57B | Avg. Daily Volume (30 days): 1,888,023 | Revenue (TTM): $4.58B |
| Net Income Margin (TTM): 18.99% | ROE (TTM): 24.30% | Net Cash: $2.38B |
| P/E: 20.06 | Forward P/E: 13.24 | EV/EBIDTA (TTM): 10.81 |
| P/S (TTM): 3.61 | P/B (TTM): 3.17 | 52 Week Range: $53.56 – $87.24 |
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