After more than two years of venture capital retrenchment, startups that survived the battle are emerging as real businesses. But their haphazard journeys — grabbing capital when and where they could — have, in many cases, made a mess of these companies’ capitalization tables.
It seems that guerilla fundraising, along with the normal chaos of crises and opportunities requiring immediate founder attention, frequently leads to a lack of accurate recordkeeping for the company’s cap table. Companies will need to remedy that situation if they want to have any hope of raising new venture capital.
2023 was the worst year for VC funding since 2017 and 2024 hasn’t been looking much stronger. With venture investors still struggling to find a new normal, companies looking to grow will require all the usual proof points: good technology, a great market opportunity, a big problem and great underlying economics.
But they also can’t show up with a cap table that looks like a Jackson Pollock painting, all chaos and uncertainty. A bad cap table — or one that clearly signals financial laxity or mismanagement — can easily be the kiss of death in a still-challenging VC funding market.
A dirty cap table is an understandable phenomenon that regularly occurs in fledgling companies where innovation, revenue growth and customer acquisition take precedence over keeping close tabs on funding rounds. It’s a mistake entrepreneurs make time and time again. But that mistake can lead to future chaos and diminished confidence among critical investors, possibly resulting in debilitating lawsuits and a lack of interest from new investors to put more money into the administrative mess that’s been created.
So, founders who successfully wheedled needed capital from various sources in various forms and on divergent terms will now need to turn their attention to an urgent cap table cleanup. If they don’t, they’ll find their options for raising new capital on acceptable terms are severely limited.
Preparing and executing a cap table cleanup is almost as much fun as surviving two years without additional capital. It’s not a task that’s particularly easy to fix in the rearview mirror, either. It’s distracting and time-consuming, but it can and must be done.
Here are the major steps:
Get all equity and capital-related documents in one place. Stock purchase agreements, option grants, SAFEs, convertible notes, term sheets, everything. Version control is important to ensure that the actual governing document is the one being compiled.
Make sure every equity issuance is reconciled with board minutes, resolutions and written consents.
Categorize all equity raises, taking care to separate common stock, preferred stock, options, warrants, SAFEs and convertible notes. Record all details for each type of equity: issue date, number of shares, price and any specific terms or conditions.
Check all ownership information and update records — shareholder names (including founders, employees, investors and advisors) — and be sure the share numbers are accurate.
Lay out the variables in the equity structure by overlaying vesting schedules for founder, employee and affiliated party equity. Also, make sure all convertible instruments are tracked with their conversion terms and schedule.
This is the time to implement cap table software, like Carta, Pulley, Shareworks and others. Empower a qualified individual or cohesive team with the duties of overseeing a well maintained cap stack with responsibility for creating and maintaining efficient workflows and controls that will deliver the results that keep you on track. Creating the foundation for future growth and complexity and are worth the investment for a growing company.
Get help where needed. No founder can spare their key team members for an extended period to perform what is in essence a heavily clerical and analytical task. A company’s accountants and outside counsel can usually make much shorter work of the task.
Communicate with investors and evaluate any obvious challenges to a fundraising process. Are approvals awkward and time-consuming? Do you have too many small investors? At least come to the process armed with the knowledge of where the challenges will be. Also, examine any disproportionate voting rights that could become hurdles to new funding.
Nailing down the cap table in many ways is the documentation of a company’s financial narrative, which in turn becomes an important element in the fundraising process.
Having a clean cap table is a statement of operational competence and managerial transparency. It says that adults are in charge and future investors and their capital will be treated with the same level of respect and professionalism.
It’s been a long, hard road for startups these past few years, and in some ways has led to permanent changes in venture capital investing. Companies that can demonstrate traditional capabilities like operating efficiency, financial control and tight business planning alongside their innovative technology development are being rewarded by investors. A squeaky clean cap table signals readiness to take investors’ capital and earn them the returns they deserve.
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I must have seen more than a thousand Chinese takeout menus. I always look at them, although I pretty much always order the same thing. Last week I noticed something that I have never seen before — a suggestion section for what to order. There were five suggestions. They all looked good and were slightly upscale. That got me thinking about whether CPAs should offer suggested services, and if not, why don’t they?
I did not order any of the suggestions on the menu as my mind was made up about what I was going to order, but the suggestions planted a seed in my mind. I suspect I will order one of them in the near future.
I liked the idea and, while I’ve never directly presented suggestions as such to a client, I have offered suggestions in the form of a listing of services that were not included in my fixed-price engagements. One example of such wording is: “Not included are services in connection with reviewing your accounting system and its controls that would offer a higher degree of protection against employee theft or embezzlement. This would be a special single purpose engagement at prices and timing to be decided upon along with a catalogue of benefits and value to be conferred upon you.”
This rarely resulted in added engagements. Perhaps a better way of presenting this, using the Chinese menu idea, would have been:
Suggestions of additional high-value single purpose services (prices fixed and guaranteed for one year):
Analysis and review of your accounting system and its controls that would offer a higher degree of protection against employee errors, theft or embezzlement: $7,200
This suggestion also provides a fixed price and a deadline for the client to engage you for this service. i.e., one year. At the point of offering this service, you should have a pretty good idea of what would be involved, how it would be staffed and the time it would take. Even if you are too low, you will still receive the added revenue, help your client with a service they need and can benefit from, open the door to further services at a later date and establish a stronger relationship with that client.
Further, if you did not offer a fixed fee, the client might have trepidation at the cost and would be hesitant to ask what it might be or for an estimate or range. In my experience, any estimate on a time-based project becomes a “fixed” fee, plus or minus 10% or 15%, so why not just quote a fixed fee? If you feel you are not able to reasonably estimate a fee for this service, then perhaps you are in the wrong business.
Here are some other suggestions of added engagements:
Special services in connection with a surprise bank reconciliation and a review of the client-prepared bank reconciliations during the previous year, including a reconciliation of any differences in the cash balance the client is working off of compared to the most recent month-end reconciled bank balance. The internal bank reconciliation procedures, and their thoroughness and timeliness, will be reviewed and changes will be suggested if we believe that is necessary. Price: $8,000.
An informal valuation of your business will be performed to determine an estimated value of your business, identification of value drivers, how a buyer would value your business, how our valuation could be used as a benchmark to measure growth in the form of value creation, and how this value would interface with your personal financial plan and estate plan. Price with a written valuation and template to measure future changes in value: $12,500. Price with the template but without the written valuation: $8,500.
An analysis of your eventual estate liquidity and cash flow based upon your present and projected individual financial statement, your estimate of the current value of your business, your estimate of your cash flow needs in retirement, a review of your will and any trust documents, designations of beneficiary forms and life insurance: Price $9,500.
The above are examples of added high-value services that could confer substantial benefit along with the client having a heightened feeling of financial security, comfort and empowerment. All prices mentioned are illustrative and would be based on the client’s situation. A client with a business with sales of $3 million would have a much lower price for a valuation than a business grossing $30 million a year. Likewise, a client with $3 million net worth would have a much less complicated financial and potential estate situation than a client with $30 million net worth along with multiple trusts, real estate and business investments.
My motive with this column is to pique your interest and imagination about what your clients might need. Examine your clients’ situations, their pain points, and expressed and unmentioned concerns, find ways to help them, and then prepare a listing of three or four suggested services that would allay their fears and concerns.
If my local Chinese restaurant could do it, then you and I should also be able to do it for our clients. Do not wait for the client to ask about added services. Suggest them now!
Do not hesitate to contact me at [email protected] with your practice management questions or about engagements you might not be able to perform.
President-elect Donald Trump said he is nominating Scott Bessent, who runs macro hedge fund Key Square Group, as the next U.S. Treasury secretary, enlisting a key adviser to manage the sweeping economic agenda he has vowed to enact in a second term.
“Scott has long been a strong advocate of the America First Agenda,” Trump said in a statement Friday. “On the eve of our Great Country’s 250th Anniversary, he will help me usher in a new Golden Age for the United States, as we fortify our position as the World’s leading Economy.”
Bessent, 62, emerged as the pick after an extended search for a Treasury chief that saw Trump consider multiple candidates — and Wall Street executives and business leaders vie to influence the president-elect’s decision. Allies believed that Trump sought a candidate that would be favored both by Wall Street as well as an electoral base eager for him to implement sweeping tariffs, embrace cryptocurrencies and crack down on undocumented migration.
Bessent beat out other prominent contenders including Apollo Global Management Inc. executive Marc Rowan, former Federal Reserve Governor Kevin Warsh and Tennessee Senator Bill Hagerty as well as Trump transition co-chair Howard Lutnick, who was named to lead the Commerce Department.not supported.
If confirmed by the Senate, Bessent would be the first openly gay Treasury chief, and one of the wealthiest in modern times. Bessent has said that he has always wanted to serve his country, but in the 1980s his sexual orientation prevented him from going to the U.S. Naval Academy, and after graduating from Yale University, from joining the State Department.
He joins an economic team beginning to take shape just weeks after Trump won a second presidential term. Trump announced that his former budget director, Russ Vought, would be returning to the same role in a statement to his social media platform later Friday.
“He did an excellent job serving in this role in my First Term – We cut four Regulations for every new Regulation, and it was a Great Success!” Trump said.
Vought, a key architect of Project 2025, the controversial Heritage Foundation policy document released during the campaign, will work alongside Bessent to implement Trump’s economic agenda.
Political thickets
As the nation’s highest ranking economic policymaker, Bessent will have to wade through political thickets in Washington, spearhead international economic diplomacy and bring Wall Street know-how to crisis situations. He will also be closely watched by investors and financial institutions, who are looking for predictability and stability.
He has been a proponent of realigning U.S. currency policy, but has stopped short of supporting an overt strategy of depreciating the dollar. During Trump’s first term, the then-president called out dollar appreciation for being harmful to US manufacturers and even considered government intervention to manage the greenback’s value.
Bessent has acknowledged that while a weaker dollar would be good for some parts of the economy, some of Trump’s proposals would drive up its value.
He has criticized President Joe Biden’s administration for its management of federal debt financing, and has talked about expanding its “friendshoring” policy to create a tiered system among trade partners.
At the Treasury, Bessent is expected to advise Trump on candidates to chair the Federal Reserve when that job opens up in May 2026. Earlier this year, he talked about the idea of nominating a new Fed chair well in advance of the expiration of current chair Jerome Powell’s term. Financial markets would turn their attention to that shadow Fed chair instead of Powell, Bessent has said.
He has said the Fed was too slow to respond to rising inflation in 2021, and criticized the US central bank for its large interest-rate cut in September.
Bessent spent part of his career managing money for billionaire George Soros. He lived in London and was part of the team, under Stan Druckenmiller, that made $1 billion in 1992 shorting the pound — a wager that helped force the currency out of the European Exchange Rate Mechanism, and made Soros famous as the man who broke the Bank of England.
He would be the second Treasury secretary, after Steven Mnuchin, who has worked for groups with close ties to Soros.
Soros’ family office made about $10 billion in profit under Bessent as investment chief, or about 13% annualized. Since then, he’s run Key Square, which started with a $2 billion investment from Soros — funds he later returned as other investors came in.
“I think he’ll be outstanding,” said Druckenmiller. “Having worked for me and George for all those years, he’s been exposed to everything a Treasury secretary has to deal with. He has a deep knowledge of markets and he’s also an intellectual who has the chops to work with academic policymakers. It’s a rare combination.”
Bessent will be returning his hedge fund clients’ capital as soon as possible after Dec. 1, according to a person familiar with his plans. Federal rules require cabinet members to develop plans to remove their potential conflicts of interest, and then follow through on them, usually within as little as 90 days.
Here’s a look at some key areas of responsibility for the role of Treasury Secretary:
Oversight, taxes
Bessent is expected to play a key role in pushing for a renewal of Trump’s 2017 tax cuts through Congress, many of which are set to expire at the end of 2025.
The Treasury chief could be charged with liaising with Republicans in Congress to expand the scope of the tax bill to include some of Trump’s campaign-trail tax promises, including a 15% corporate rate and exempting tipped wages from taxation.
The Treasury Secretary is also charged with running the Financial Stability Oversight Council, a panel set up after the financial crisis. Under outgoing Treasury Secretary Janet Yellen, FSOC looked at the issue of climate change, triggering criticism from Republicans who have been wary of any requirement for banks to incorporate climate in their lending or capital decisions.
FSOC under Yellen also recommended stronger oversight of stablecoins, which the Fed has likened to bank deposits and money market funds — and which are subject to much more regulation. Trump’s advocacy of the crypto space on the campaign trail likely will put the new Treasury chief’s stance under the spotlight.
Economic diplomacy
Peppered through the year are meetings of the finance chiefs of the Group of Seven, G-20 and other international organizations, which the Treasury secretary typically attends as the chief U.S. representative.
The Treasury Department implements U.S. sanctions on foreign countries, companies and individuals, which have soared in number over the past several years. Yellen helped to lead efforts at the G-7 to isolate Russia after its full-scale invasion of Ukraine, and to step up financial assistance for Kyiv.
The secretary also has often served as point person on engagement with China. The Treasury chief tends to be a cautionary voice when it comes to proposals aimed at America’s biggest strategic rival. Mnuchin, Trump’s Treasury head in his first term, was seen as playing that role when tensions escalated in 2018 and 2019.
Debt management
In charge of the nation’s purse strings, Bessent will have to deal with a costly, and ballooning, debt load. The federal budget deficit crept up to 6.4% of GDP in fiscal 2024, historically high for a time of economic expansion and full employment. A key driver has been soaring interest costs, in the wake of Fed rate hikes in 2022 and 2023.
“No one has been more terrified about this debt stack and the coming refinance we’ve got to do,” Bessent said on a recent War Roompodcast with longtime Trump adviser Stephen Bannon. What can “stabilize the bond market” is a fiscal package that reins in spending, he said.
Bessent has also complained about the Treasury’s debt financing strategy, claiming that Yellen was trying to juice the economy and help her boss ahead of the November election — a charge she rejected.
Debt managers may need to be active in managing the Treasury’s liquidity, because the federal debt ceiling is scheduled to kick back in at the start of January. That bars the department from issuing new debt, and triggers an oft-deployed sequence of maneuvers to prevent the U.S. government from running out of cash or, worse, defaulting on its debt — an event that could have catastrophic repercussions.
Glen Capelo, who spent more than three decades on Wall Street bond-trading desks and is now a managing director at Mischler Financial Group, called Bessent a “fiscal hawk.”
“He definitely will be positive overall for the economy and the markets. He wants to rein in spending. Bessent wants to get the Secretary of the Treasury back in line with the markets – because he does believe Janet Yellen has twisted the issuance around a bit,” Capelo said.
Macy’s Inc. said it would delay its third-quarter earnings release after an investigation revealed an employee hid more than $100 million of expenses.
An employee “intentionally” made erroneous accounting accrual entries to hide about $132 million to $154 million of cumulative delivery expenses stretching over multiple years, the company said Monday.
The worker, who was responsible for small package delivery expense accounting, is no longer employed with the company.
The retailer said it identified an issue with its delivery expenses while it was preparing its quarterly financial statements, prompting the initiation of an independent investigation. The probe revealed a single employee hid the expenses from the fourth quarter of 2021 through the fiscal quarter ended Nov. 2, 2024.
Macy’s shares fell 4% in Monday trading in New York. The stock had lost 19% this year through Friday’s close as Wall Street remains skeptical of Spring’s plan to close poorly performing stores and boost sales at its top locations.
The company said there’s “no indication” the erroneous accounting accrual entries had any impact on the company’s cash management activities or vendor payments.
Macy’s was slated to release its earnings report and hold a call with analysts on Tuesday. It said it will issue the release, as well as its fourth quarter and full-year outlooks, by Dec. 11.
Sales drop
Comparable sales at the retailer’s owned and licensed stores during the third quarter dropped 1.3%, according to preliminary results, slightly better than analyst expectations. The picture was rosier at Bloomingdales, where third-quarter comparable sales rose 3.2%, and at Bluemercury, which showed a 3.3% increase on an owned basis. Chief Executive Tony Spring, who took over in February, said November comparable sales are “trending ahead” of third-quarter levels across its various brands.
Third-quarter sales fell 2.4% to $4.74 billion, below Wall Street estimates.
“While we work diligently to complete the investigation as soon as practicable and ensure this matter is handled appropriately, our colleagues across the company are focused on serving our customers and executing our strategy for a successful holiday season,” Spring said.
As the largest department-store chain in the U.S. by revenue, Macy’s often serves as a barometer of mass-market consumer spending during the all-important holiday season. A delay of earnings until after the annual Black Friday shopping extravaganza may provide investors with a deeper look into holiday spending trends.
While the accounting issue and the delay in earnings isn’t good, “the scope of the issue doesn’t seem terribly alarming,” a Vital Knowledge note said.
Still, the incident — and the fact that the accounting errors go back to 2021 — “raises the question as to the competence of the company’s auditors,” wrote Neil Saunders, managing director at GlobalData.
“Such things create more nervousness for investors who are already concerned about the company’s performance,” he added.