Immad Akhund on Mercury, Angel Investing and His New Fund

Harry Stebbings interviews Mercury CEO and angel investor Immad Akhund about startup investing, fundraising and building a financial-services company. Akhund announces a $26 million institutional fund with partner Yash Toshi, an earlier Mercury investor. He remains Mercury's CEO and has direct interests in the company, the fund and several businesses he discusses.

Akhund says he has made around 350 angel investments since 2016, previously using an AngelList rolling fund, and that the new fund had already invested in five or six companies. These are his figures at the time of the interview, not a complete audited track record. The new institutional fund and earlier angel investments are distinct.

His first lesson is not to impose his own idea on a founder. As an operator he initially wanted to be hands-on, but realized investors are accompanying someone else's journey. He cites Rappi, where he says he invested early and had little subsequent contact as the company grew; a private valuation milestone is not itself cash returned.

Stebbings says a founder who accepts an investor's suggestion too readily can be a red flag. Akhund says he previously missed opportunities by expecting inexperienced founders to challenge him like seasoned executives: young people may be intimidated in investor meetings. He suggests judging the person in context rather than treating one interaction as decisive.

Akhund says strong founders may not need investors day to day, but can benefit from occasional advice. At Mercury he consulted founder-investors on hiring a CFO and fundraising terms. He values the individual partner and founder network more than generic venture-platform services, and discloses Andreessen Horowitz as Mercury's seed investor.

Sequoia's investment in Mercury's Series C mattered personally because Akhund had long sought its backing after earlier rejections. He says the firm did extensive customer and data-room diligence, even though its partner later told him she had strong early conviction. His praise is from a founder whose company received the investment.

Asked about valuation, Akhund says Sequoia's final offer was highest, though he might have accepted slightly less for a strong long-term partner. He recalls Mercury raising $120 million in its 2021 Series B at about 120 times revenue and says he would do it again. That is a financing multiple at the time, not an investment return.

His advice is to raise enough capital at a high valuation to have time to grow into it, then resist spending merely because it is available. Stebbings challenges this, arguing younger founders may spend too quickly. Akhund agrees the discipline is hard and says investors can also encourage excessive spending.

Asked about his biggest angel win that returned money, Akhund names Truebill. He recalls investing at around a $16 million valuation, the company exiting for $1.25 billion, and receiving more than a 30-times multiple over roughly 2016–21. The multiple is his account of that investment, not a fund-wide or independently audited return; exact net terms are not given.

Akhund favors repeat founders, particularly those with something left to prove, and cites his investments in Truebill and Rippling. He says his own previous company exited for $45 million after four pivots and he still wanted to build something larger. His preference is a selection bias and does not show first-time founders cannot succeed.

He says entering a market without prior industry experience can also help: before Mercury he did not know banking deeply, and some specialist fintech funds focused on obstacles rather than investing. Andreessen Horowitz led the seed round, and fintech founders also backed him. This is his interpretation of those decisions, not a general rule about expertise.

Akhund recalls passing on Scale AI partly because its founders were very young and says that was a mistake. He now tries to account for how intimidating investor meetings can be and the ability of young founders to grow. He does not present a complete list of misses or their investment outcomes.

For aspiring angels, he says a portfolio of at least 20 to 30 investments can support learning and diversification, rather than relying on a handful of bets. He notes that angel investing requires money one can afford to commit. Diversification does not guarantee a return; his suggested portfolio size reflects his strategy.

At higher seed entry valuations, he says a company reaching a $1 billion valuation can produce very different multiples after dilution, citing examples from around eight to 30 or 40 times. He wants an outsized fund outcome and says some investments need far larger outcomes. A private-company valuation is not necessarily an exit or realized cash return.

Akhund says deal flow improved as founders referred him and as Mercury grew, though he cannot cleanly separate his reputation as an angel from his standing as a founder. He recalls selling some secondary shares in one investment and wishing in hindsight he had sold more. His choice to hold others is a personal investment decision.

He cites Airtable as a company he thinks could eventually reach $50 billion, based on its founder, data and AI applications. Stebbings challenges the revenue required to justify such a valuation. Akhund is an investor in Airtable; the suggested valuation and growth are a bullish scenario, not realized performance.

On AI products that replace labor, Akhund expects competition to compress pricing after initial sales based on a fraction of labor costs. He contrasts that with coding subscriptions he believes can retain users through value and workflow. These are market forecasts; the interview supplies no comparable margins or retention data to establish either outcome.

Stebbings asks whether switching between AI coding products means defensibility has disappeared. Akhund expects experimentation and churn now, followed by more established brands, integrated products and enterprise relationships. He says Cursor is the most common coding tool he hears about inside Mercury; these are impressions rather than a measured competitive study.

Asked whether Mercury will have more or fewer engineers in five years, he expects more: productivity gains could enable the company to pursue more work. This is a company leader's forecast, not a guarantee for individual employees or the wider labor market.

Akhund regrets waiting until 2022 to launch Mercury's credit card. He says he initially focused on banking while competitors developed cards and banking products, and believes a launch around 2020 was possible. He claims Mercury's card is now dominant among its own customers; that is a company-specific assertion, not an independent market-share statistic.

He says competitors have appeared threatening throughout his career, but prefers focusing on customers and a long-term product vision rather than copying rivals. Stebbings points to counterpositioning as an alternative; Akhund says that approach does not personally resonate with him. Their disagreement reflects different strategic lenses.

Akhund says Mercury has more than 200,000 customers and focuses on businesses from inception, while competitors may serve larger enterprises. Stebbings asks why others command higher valuations. Akhund says different businesses and markets can be valued differently; customer numbers, valuations and revenue are not interchangeable, and his competitive claims are not independently verified.

Akhund gives several reasons for creating the institutional fund: some limited partners preferred a conventional fund to the rolling vehicle, and his deal flow had outgrown what he could review alone. He credits Mercury's reach for access to founders and says working with Toshi helps. The fund could benefit commercially from his operating role.

The plan is a diversified portfolio of about 60 companies, mostly non-lead investments averaging around $150,000 initially. He says some higher-conviction checks could be larger and the fund will retain selective reserves. The simple 60-times-$150,000 calculation is $9 million of initial checks, not a complete allocation of the $26 million fund.

Stebbings advises avoiding reserves and using special-purpose vehicles for follow-on investments. Akhund prefers selective reserves, saying founders may not like SPVs and that some are driven by fear of missing out. Stebbings argues a timely vehicle from a trusted investor can work; they disagree on fund design rather than demonstrate which will earn more.

Akhund says early progress can reveal promising companies within months, but Stebbings counters that several of his own successful investments were slow starts. Akhund acknowledges that six months may be too early and says existing investors can sometimes see progress before outsiders. Neither view guarantees an investor can identify winners early.

He says he has avoided some AI seed deals because of repeated pitches and high valuations, but notes that four of his last eight investments were AI. He looks for deep domain expertise or convincing traction rather than AI for its own sake. This is his selection approach, and the portfolio figures are a snapshot he provides.

In space technology, Akhund describes learning by making a few investments and speaking with founders. He names Stoke Space and Albedo and discusses launch, imagery and communications as markets. He says seed pricing can be less competitive than AI software; his assessments reflect investments and are not independent technical or market valuations.

Asked how he will support 60 companies while running Mercury, Akhund says founders generally ask for relatively little time and he often helps in short conversations. He enjoys those interactions and says he speaks to entrepreneurs several times a week. This is his account of capacity, not evidence every founder will receive the same level of support.

He says small non-lead checks make it easier to join rounds led by larger funds. He enjoys selecting companies and cites an investment in Etched as an example of learning about a new field. His description of access and selection is a fund manager's claim, not proof of superior future returns.

Akhund says core fund commitments took about three weeks to secure, while negotiating the limited partnership agreement took around a month and a half. He says the largest commitment was $7.5 million and roughly 60% came from funds of funds, with entrepreneurs and general partners comprising much of the rest. These are his fundraising figures.

Stebbings challenges the potential conflict of a founder raising company capital and separately managing outside limited partners' money. Akhund says he has been transparent that Mercury is his main job and that his investing preceded the company. He says his co-founders support the arrangement; disclosure does not itself resolve every possible conflict.

Akhund estimates the first 30 Mercury alpha customers were companies he had invested in. He argues his network helps Mercury and Mercury's success helps his fund access deals, particularly in B2B and fintech. This makes the mutual commercial interest explicit; the interview does not examine individual allocation or customer-conflict policies.

Asked why he needs outside capital rather than selling Mercury shares to invest personally, he says he enjoys building an institution with a partner and wants to support more founders. He leaves open how the first fund may develop, including larger checks or incubation. Those are possibilities, not promises or demonstrated returns.

Stebbings argues large multi-stage firms make seed investing difficult. Akhund says his small non-lead strategy can invest alongside them and that different founders may fall outside large funds' preferred profiles. Both speak as investors with their own business models.

Akhund predicts some large multi-stage funds will become public and more capital will enter venture, while acknowledging a current liquidity shortage. He thinks small specialist and large multi-stage firms may fare better than those in the middle. This is a forecast about fund structure, not evidence of future returns.

On IPOs, he says public-market costs and limited attention to smaller companies encourage firms to remain private longer. He wants Mercury to become a long-term company and sees a public listing as eventually plausible, but does not set a date. His claims about public-market structure are opinions, not a complete analysis.

He says Mercury recently offered an employee tender and that some early employees and investors had sold secondaries since 2021. He supports giving employees a viable liquidity option rather than making equity entirely dependent on an eventual IPO. A secondary sale provides liquidity to a seller but is not the same as new capital raised by the company.

Stebbings names Elad Gil as a trusted source of deals. Akhund praises 50 Years and Better Tomorrow Ventures, disclosing that he is an LP in 50 Years. He says he likes receiving ideas from specialists who know a field well, even though he prefers a broad strategy for his own investing.

In quick fire, Akhund says rapid AI progress has made him more open to advanced superintelligence arriving sooner than he previously thought, while remaining uncertain about a five-year timeline. He uses ChatGPT as a thinking and presentation aid. The timing is speculative, not a technical conclusion established by the interview.

He says Mercury wrote down six cultural attributes at the start and uses interview questions and internal practices to reinforce them. One example is favoring humility even when that means passing on a highly accomplished executive. His claim of a cohesive culture is a company leader's assessment.

Looking back, Akhund says Mercury raised too much in its seed round: he recalls $6 million at a $23 million valuation and substantial dilution. He estimates $3.5 million might have provided enough runway, while acknowledging he did not know the company would launch successfully. That is a hindsight counterfactual, not a recommendation to every founder.

Asked for a bullish case for a $100 billion Mercury, he argues banking and financial software could become one integrated customer experience. He cites large market-size estimates and sees opportunities beyond the US. This is a founder's long-term scenario, not an independently verified market forecast or guarantee of company value.