Books on Startups, Founders, Investors

Entrepreneurs know the tradeoffs of external capital. The money enables faster growth and infrastructure, but the price is control and occasional chaos. In these 12 books, founders, investors, and academics share the good and the bad.

World Eaters: How Venture Capital Is Cannibalizing the Economy

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World Eaters

by Catherine Bracy

Bracy, founder of the nonprofit organization TechEquity, contends that the venture capital model of “hyper maximalist growth” has far-reaching negative impact and isn’t a good fit for most startups. Congressman Ro Khanna calls the book “important and insightful,” while Publishers Weekly says it’s a “convincing call for change.”

Raising Capital with Confidence

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Raising Capital with Confidence

by Darin H Mangum, Esq.

The author leads a law firm specializing in securities, with clients including private investment firms and funds. He explains deal structures, how to find the right investors, legal compliance, and more, offering a practical guide to help readers avoid common financing pitfalls and meet their unique business needs for sustainable growth.

The Startup Lifecycle: The Definitive Guide to Building a Startup from Idea to Exit

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The Startup Lifecycle

by Gregory Shepard

According to Shepard, nine out of 10 startups fail within five years, often due to common and avoidable mistakes. He has built and sold a dozen businesses and provides a roadmap to every phase of the startup lifecycle, from initial vision through growth and successful exit.

Start. Scale. Exit. Repeat. Serial Entrepreneurs’ Secrets Revealed!

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Start. Scale. Exit. Repeat.

by Colin C. Campbell

Campbell combines his decades of experience as a serial entrepreneur with insights distilled from interviewing more than 30 entrepreneurs and experts to create a multi-award-winning guide to building, growing, and selling a business.

Exit-Ready Marketing: The 9-Step Framework to Maximize Your Valuation

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Exit-Ready Marketing

by Shiv Narayanan

Unpredictable revenue can be an obstacle to attracting investment. Narayanan focuses on simple but sophisticated data-driven marketing strategies that create predictable revenue necessary for planning and investing in your business’s growth and increasing its value to private equity investors.

The Venture Mindset: How to Make Smarter Bets and Achieve Extraordinary Growth

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The Venture Mindset

by Ilya Strebulaev, Alex Dang

Strebulaev is the leading academic on venture capital; Dang is a senior tech executive, having worked at firms such as McKinsey and Amazon. In this national bestseller, they share key venture capital principles to improve decision-making, identify emerging trends and opportunities, and spark innovation.

Behind the Startup: How Venture Capital Shapes Work, Innovation, Inequality

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Behind the Startup

by Benjamin Shestakofsky

The author, a sociologist, spent a year and a half conducting experiential research inside a successful Silicon Valley startup. He explores how the intense pressure from funders to scale rapidly creates problems for the organization and, ultimately, society at large.

Founder vs Investor: The Honest Truth about Venture Capital

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Founder vs Investor

by Elizabeth Joy Zalman and Jerry Neumann

A two-time founder and a veteran venture capital investor reveal an insider’s view of how the differing motives and incentives of founders and investors — “those with the vision and those with the money” — often result in chaos in the early stages of fast-growing startups.

Two and Twenty: How the Masters of Private Equity Always Win

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Two and Twenty

by Sachin Khajuria

Once an investing niche, private equity now has a vast global influence. The author, a former partner at a leading private equity firm and longtime investor, offers what Fortune calls “a true insider’s account of the industry” through stories of real-life dealmaking.

The Power Law: Venture Capital and the Making of the New Future

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The Power Law

by Sebastian Mallaby

Mallaby, a bestselling author and two-time Pulitzer finalist, examines how the nature of venture capital shapes innovation in Silicon Valley and beyond. He delves into the lesser-known aspects of the success and failure of firms such as Apple, Uber, and WeWork, blending storytelling and analysis.

Super Founders: What Data Reveals About Billion-Dollar Startups

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Super Founders

by Ali Tamaseb

Tamaseb interviews top founders and investors, and shares inside stories from PayPal, Instacart, Sequoia Capital, Lyft, Founders Fund, ByteDance, and SpaceX, among others. The result is surprising revelations — for example, being first to market with an idea isn’t necessary for success.

Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist 4th Edition

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Venture Deals

by Brad Feld, Jason Mendelson

The authors have decades of experience as entrepreneurs, investors, and mentors to founders. Drawing on their involvement in scores of venture financings, they explain term sheets, negotiating strategies, legal considerations, types of debt, and how to build supportive and collaborative relationships between entrepreneurs and investors.

Revenue Loans Are Fast Cash at a Price

A growing form of revenue-based financing can fund the marketing push or inventory boost for ecommerce merchants to capture growth opportunities. But “merchant cash advances” are often expensive and not suited to every business.

Ecommerce companies experience highs and lows. Merchant cash advances tend to work better when merchants are on the upswing.

A merchant cash advance (MCA) is a loan, a lump-sum payment, that the borrower agrees to repay through a fixed percentage of revenue.

According to Aidan Corbett, CEO of Wayflyer, an MCA and term-loan provider, three characteristics distinguish MCAs from other types of financing:

  • Aligned outcomes between the lender and merchant,
  • Revenue-based repayment,
  • Speed and ease of approval.

Each can be beneficial, but with trade-offs.

Screenshot of Wayflyer's home page

Wayflyer offers merchant cash advances, as do Shopify Capital, Stripe Capital, and others.

Aligned incentives

MCAs differ from a traditional lender-borrower dynamic. The provider’s repayment depends on the merchant’s revenue performance. Both have a shared interest in success.

“I’m being careful not to say borrower and lender,” Corbett said, emphasizing that both sides benefit only if the merchant performs well.

In the United States, MCAs are typically unsecured and unregulated. If a business fails outright, the company providing the advance may lose its investment. MCA funders look for healthy, growing businesses.

The idea of aligned outcomes is a newer trend. Past MCAs resembled payday loans, but the best 2025 offerings emphasize a partnership model aimed at sustainable growth with transparent fees.

Revenue-based repayment

Borrowers repay MCAs through a share of daily or weekly sales, not fixed monthly payments. The share varies but is typically 10% to 25% according to published reports.

Corbett gave the example of an ecommerce company receiving a $100,000 advance. The repayment might total $106,000, with the $6,000 difference representing the provider’s fee. If daily sales are strong, the repayment is quick. If sales dip, the repayments slow down.

This structure is appealing to ecommerce shops with predictable, growing revenue. But it also means that repayment can begin before the business reaps the monetary benefit of the borrowed capital, especially for inventory or long-term marketing campaigns.

Fast approval

MCAs are fast. Ecommerce businesses can qualify within days after providing sales history and a plan for using the funds. There is typically no collateral requirement and no formal credit check.

Corbett said Wayflyer looks for growing brands with a broad product mix and high reorder rates. Stores with strong and consistent return on ad spend and efficient customer acquisition tactics are also favorable candidates.

MCA Use Case

Consider an ecommerce company selling home organization products with steady, year-round revenue. The company recently launched a new line of modular storage kits. Initial customer response is strong. Conversion rates are up, and test campaigns are returning a 4:1 ROAS.

A home improvement blog with more than 500,000 readers offers the business a two-week premium ad placement. The channel that has worked well for the merchant, but the $30,000 ad buy is time-sensitive, and the company doesn’t have the cash on hand.

A traditional loan won’t arrive in time. Instead, the founder uses a $30,000 MCA, agreeing to repay $36,000 via daily deductions from revenue.

The estimated boost in customer acquisition and long-term customer value more than offsets the financing cost.

It’s a good use case. The MCA funds a specific, high-return opportunity with relatively predictable payback.

Costs

MCA fees — “factor rates”— can be high. For instance, a factor rate of 1.2 on a $50,000 advance means the merchant owes $60,000 in total, regardless of the repayment period. A six-month payback can exceed 24% effective annual interest.

Still, Corbett said the MCA market for ecommerce has grown more competitive, and some providers now offer rates comparable to term loans, particularly for strong companies.

He advises merchants to shop around, avoid excessive origination fees, and never take an MCA with exorbitant effective interest. Fast money should not outweigh sound financial planning.

Dependency

MCAs can reduce cash flow before earnings materialize. Because repayments are tied to revenue, not profit, they can erode margins quickly.

Consider an ecommerce store with a 35% gross margin. If customer acquisition costs are 10%, payment processing fees are 2%, and the MCA repayment rate is 20%, the business retains just a 3% margin.

That razor-thin gross profit makes it difficult to self-fund growth or even cover operating expenses. The merchant may then rely on successive MCAs, falling into a cycle of borrowing.

Nonetheless, used strategically, MCAs can fund timely opportunities for growth. Thanks to Wayflyer, Shopify Capital, Stripe Capital, and similar firms, MCAs are increasingly common and beneficial.

Charts: U.S. Banking Technology Trends

KPMG’s annual U.S. banking technology survey is a “pulse-check of the priorities of leadership across the industry.” For 2025, the accounting and consulting firm queried 200 U.S. banking executives from large and small institutions across various departments to assess their tech expertise, investment plans, and readiness for inevitable change.

The firm then assembled the findings in its “2025 Banking Technology Survey” report issued in April.

Per the KPMG report, U.S. banking executives are adopting generative AI across the entire company, seeing it as essential to their long-term relevance.

Moreover, 42% of respondents believe that by the end of 2025, genAI will handle 21% to 40% of daily tasks, allowing employees to focus more on higher-value work.

Furthermore, most banks are upgrading their payments platforms, reflecting the preferences of today’s consumers.

Ecommerce Investor on Turnaround Tactics

Mehtab Bhogal is the co-founder of Karta Ventures, a Canada-based acquirer of troubled ecommerce businesses. The firm seeks companies with “issues,” such as unpaid taxes, regulatory problems, and founder disputes.

He says buying distressed companies is like salvaging a crashed car. “What are the parts worth?” he asks.

Mehtab and I recently spoke. He addressed identifying hidden value, turnaround tactics, seller concerns, and more.

The entire audio of our conversation is embedded below. The transcript is edited for clarity and length.

Eric Bandholz: Give us a quick rundown.

Mehtab Bhogal: I’m the co-founder of Karta Ventures. We invest in consumer brands in distressed situations, such as tax issues, regulatory problems, founder disputes, things like that. We move fast and write checks quickly. Our portfolio ranges from a direct-to-consumer succulent plant farm to traditional apparel companies.

Early on, we invested in companies with both income statement and balance sheet problems. Now, I prefer one or the other. We focus on size. We will shrink a company if necessary. An optimal size for us is scaling businesses down to $15-$20 million in annual D2C revenue if we’re buying them outright.

For example, we looked at a retailer once that had peaked at $110 million, was doing $70 million, but we believed it operated most profitably at $30–$40 million in revenue.

Bandholz: How do you find the right deals?

Bhogal: In 2018, when we began, we sent cold emails to over 2,000 companies. We used BuiltWith to analyze tech stacks and backends to estimate revenue. From there, we targeted businesses generating a few million annually. Most of our deal flow now comes from word of mouth, especially since other investors tend to avoid turnarounds.

We also invest in profitable companies with big projects. One company needed help building a new manufacturing facility, which we’re good at. If there’s value to unlock, we’re interested.

Buying distressed companies is like salvaging a crashed car: What are the parts worth, and what could a skilled mechanic do with them? We sometimes acquire the right to buy equity before full diligence. That lets us move quickly, cut costs, and create breathing room while we dig deeper. We often reduce expenses by six to seven figures within a week or so. Meanwhile, we gain insights, and the existing management determines if they want to work with us.

Bandholz: How can you make those cuts in a single week?

Bhogal: It’s all about context. We can usually tell whether growth came from good marketing or a great product.

For example, I know a founder doing 30% net margins on $30-40 million in annual revenue. He has no idea what he’s doing on the ecommerce side. But his product is incredible — strong patents, hard to copy, perfect market fit. That’s why it works.

We’ve developed pattern recognition from working with many companies. We spot inefficiencies quickly, such as bloated teams, sloppy ad accounts, and underutilized staff. For instance, if a company needs only four raw materials, why does it have an entire supply chain team?

Or why does a CFO at a $20 million company have a huge support staff?

Founders are sometimes great at marketing but weak at finance or operations. I can log into a Google Ads account and quickly see if targeting and spend are optimized. That’s the type of stuff we jump on fast.

Bandholz: Is your goal to flip a business or hold it?

Bhogal: It depends. Sometimes we buy the business outright; other times we invest as minority shareholders with no control — both models work for us.

Take the succulent plant business we invested in back in 2018. We helped restructure debt, acquired a farm to integrate vertically, and began growing and shipping plants ourselves from Riverside, California. We’ve held that position and won’t exit unless the founder wants to. That was our agreement — get our cash out in one to two years and go from there.

Other founders want to optimize and sell in 6-12 months. That works too. The key is alignment: Everyone should have the same end goal and roadmap. If those are in place, things rarely go wrong.

Bandholz: What’s your daily focus, researching deals or operating businesses?

Bhogal: We’re hands-on. We teach teams how to manage recurring tasks. But for one-off strategic decisions, such as evaluating whether to use a 3PL or in-house fulfillment, we’re directly involved. The same goes for setting up manufacturing or optimizing marketing. We’ve performed those analyses so many times that we can quickly run the numbers.

We don’t want to be in the weeds long-term, but we’ll dive in initially to gain clarity and speed things up. We want the company to operate without needing our daily involvement. But we’re very engaged for the first few months.

Bandholz: How should founders evaluate debt financing?

Bhogal: First, understand the deal. Model your payments and liabilities. Know if there’s a personal guarantee, if the loan is secured, and what happens if revenue dips. Research lenders on PACER to review their legal history — some are reputable, others not so much. Ecommerce lenders, in particular, can be volatile. Many raised venture money and spent it recklessly.

Ask yourself: Where is this lender getting its money? Is it sustainable, or will its problems become yours in a downturn? In uncertain consumer markets, flexibility matters. We’d rather pay more for a dependable, traditional lender than risk a deal that could backfire if the economy shifts.

Bandholz: Where can people contact you?

Bhogal: Our site is KartaVentures.com. I’m on X and LinkedIn.

Charts: Global M&A Trends Q4 2024

The deal value of global 2024 mergers and acquisitions transactions was up 15% year-over-year as of early December and on pace to reach about $3.5 trillion for the year. That’s according to Bain & Company’s new “Global M&A Report 2025” (PDF), which recaps 2024 activity based on data from Deallogic and S&P Capital IQ.

According to the Bain report, in 2024, deal value was historically low relative to global GDP, but the outlook for 2025 is strong as acquistions and divestitures become essential for companies navigating technological disruption.

The report also shows that most global industries grew or remained stable in 2024, with Energy and Natural Resources topping the list, followed by Advanced Manufacturing and Services.

Bain & Company also surveyed 307 M&A executive practitioners in October 2024 across the U.S., Australia, Brazil, Canada, France, Germany, India, Italy, Japan, and the U.K. — inquiring about their use of generative AI to enhance deal-making.

BNPL Fuels Supplier, Retailer Growth

Buy-now pay-later loans can boost cash flow for wholesalers and retailers in 2025 and beyond.

Business-to-business sales bring to mind massive deals with million-dollar transactions, but many wholesale brands sell to small retailers, where deals are in the thousands, not millions.

“We have a few different sock brands running on Cin7, and they sell to kiosks and small shops,” said Ajoy Krishnamoorthy, the CEO of Cin7, which makes cloud-based inventory management software, in an email exchange.

“Those retailers place orders that are $1,000 or $10,000 worth and are often seasonally driven — perfect for BNPL,” stated Krishnamoorthy.

Cash Flow

In particular, BNPL for B2B may be a cash flow opportunity for both the supplier and retailer.

For wholesalers, BNPL accelerates cash inflows and reduces credit risk. For retailers, it aligns inventory costs with revenue, provides financial breathing room, and facilitates growth. Both parties benefit, making BNPL a powerful tool in modern B2B commerce.

Wholesalers

Cash flow is essential for manufacturers, brands, and distributors.

The trouble is that many often wait to get paid. Traditional trade credit arrangements have 30-, 60-, or 90-day terms. B2B BNPL addresses the issue by delivering the payment in a few days or less.

Imagine how much more a manufacturer could produce if a $10,000 invoice is paid tomorrow instead of 60 days from now. The business could rapidly reinvest, explore new marketers, or expand its product line.

BNPL mitigates credit risk. Wholesalers that extend trade credit to retailers are exposed to potential late payments or defaults.

Yet BNPL’s advantages come with a cost: loan fees of 3% or more, typically. Sellers can pay the fees or pass them to buyers. Regardless, there is a cost in money or customer relationships.

Retailers

Cash flow is also vital for retailers operating on thin margins. BNPL loans usually offer better rates than credit cards and are relatively more accessible than advances from a bank or finance company.

Loan Feature BNPL Loans Credit Cards Capital Loans
Approval speed Instant or rapid Moderate Slow
Interest rates Often 0% short term 15%-25% 4%-10%
Flexibility High, purchase-specific High, general purpose Low, long-term use
Default risk Low Moderate High

BNPL loans also offer flexibility. Imagine a small sock seller like the one Krishnamoorthy described. The seller decides to augment its online revenue with a kiosk at the local mall but doesn’t know how to forecast inventory needs.

With a BNPL loan, the merchant could purchase for the kiosk, say, five months’ worth of socks for its ecommerce shop. If the new mall location works well and the socks sell out, it is easy to pay off the loan early. If not, the seller can make monthly payments and sell the inventory online.

The interest rate will almost certainly be lower than a revolving charge card.

The example need not be a physical location. BNPL’s flexible payment terms and rapid application process could fuel new online opportunities.

The risk is relatively low, too. Missing a BNPL loan payment may result in penalties but generally avoids the high compounding interest of credit cards.

Finally, the merchant could generate revenue as the merchandise sells — the BNPL loan improves cash flow.

As with any form of credit, BNPL could be abused or misused.

BNPL for B2B

With its potential benefits, BNPL for B2B will likely accelerate in 2025. I’ve seen estimates of 27% growth this year, roughly mirroring the 25% growth projection for B2C.

Charts: Global Investor Trends 2024

For its fourth annual “Global Investor Survey,” PwC queried 345 global investors and analysts in September 2024 across various regions, asset classes, and investment approaches. The goal was to understand respondents’ expectations for the companies they invest in and cover and their views on risks and technology, including generative AI.

Thirty-six percent of respondents replied the companies they own or cover are “highly” or “extremely” exposed to geopolitical conflict and cyber risk.

Investors emphasized the importance of companies adapting business modelsTechnological change was the top priority, followed by government regulation, shifts in customer preferences, and supply chain instability.

Generative AI will drive significant performance gains without compromising employees’ roles, according to the respondents. Sixty-six percent expect the companies they invest in to achieve productivity boosts from AI within the next year, while 63% foresee revenue growth and 62% predict increased profitability.

Moreover, the data also shows that investors are more inclined to view AI as an opportunity rather than a challenge.

Charts: Tech Impact on Global Fund Managers, Q4 2024

Eighty-four percent of surveyed asset managers and investors say that disruptive technologies are enhancing operating efficiency, a figure closely matched by those noting improvement in revenue (80%). That’s according to PwC’s 2024 asset and wealth management report titled, “Unleashing the transformative power of disruptive technology.”

The report, released in November 2024, features insights from 264 asset managers and 257 institutional investors from across 28 countries and territories and highlights how disruptive technologies are transforming investor expectations, driving innovation, and opening new markets.


The PwC report estimates global assets under management held by asset and wealth managers will hit $171 trillion by 2028.

In addition, investors continue to show a growing interest in digital assets and cryptocurrencies.

Moreover, when asked which disruptive technologies would transform wealth management in the years ahead, asset managers and institutional investors highlighted artificial intelligence, generative AI, cloud infrastructure, big data, and blockchain.

Charts: Global M&A Activity, H1 2024

In the first half of 2024, the total value of global mergers and acquisitions increased by 5% to $1.3 trillion compared to the same period in 2023. But the number of transactions — roughly 23,000 — dropped by 25%, continuing the decline that began in 2022. That’s according to PwC’s ” 2024 Mid-Year Outlook: Global M&A Industry Trends.”

According to the PwC report, in the first six months of 2024, the Asia Pacific region saw a 17% drop in deal volume and a 32% decline in value compared to the same period in 2023.

In the first half of 2024, M&A deal volume in Europe, the Middle East, and Africa (EMEA) dropped by 26%. Although deal values ​​rose by 9% compared to the previous year, they remain lower than in the pandemic and before.

Moreover, deal volumes in the Americas fell by 30% in the first half. However, values ​​rose by 22% year-over-year, primarily driven by activity in the technology and energy sectors.

Overstock Relaunches: Q2 2024 Recap

Back in 2009 I queried a marketing contact at Overstock.com about possibly interviewing Patrick Byrne, the CEO. “I’ll ask him,” the contact replied.

An hour or two later, I received an email — from Patrick Byrne.

The dialog and subsequent interview are memorable. He involved no public relations personnel — unusual for a publicly traded company — and required no preparation.

“Should I send my questions in advance?” I asked.

“No,” he said. “Ask whatever you want.”

We published the interview in December of that year. I learned he held a Stanford PhD and funded the construction of schools worldwide. He shared in the interview helpful ecommerce tips on holiday selling and shipping and was generous with his time, utterly unpretentious.

None of that squared with the Patrick Byrne years afterward, the one embroiled in nonstop investor lawsuits, who reportedly romanced a Russian spy, and, yes, the man scheming in the Trump Oval Office.

Bed Bath & Beyond

Nonetheless, I think of Byrne and the years-ago interview when Overstock makes the news, such as last year when it purchased Bed Bath & Beyond, the retail chain, out of bankruptcy.

Byrne had long since left the company. His successors evidently sought a post-pandemic reset and paid $21 million for whatever was left of the storied retailer. Thus began a disastrous chain of events.

  • June 2023: Purchased Bed Bath & Beyond.
  • October 2023: Rebranded “Overstock.com” to “BedBathAndBeyond.com.” Changed the corporate name to “Beyond, Inc.” and switched from the Nasdaq to the New York Stock Exchange with a new trading symbol of “BYON.”
  • February 2024: Posted 2023 net losses of $307.8 million, a company record, on revenue of $1.56 billion, a 20% year-over-year decline.
  • March 2024: Relaunched Overstock.com.

Q2 2024 Financials

By June 30, Beyond, Inc. operated two ecommerce sites, BedBathAndBeyond.com (housewares) and Overstock.com (discounted goods).

The Q2 financial statements do not segregate each site’s performance. Combined, the sites generated roughly $398 million of revenue for the quarter, a 5.7% decline from the previous year, with a net loss of approximately $43 million, a 42% improvement from the Q2 2023 loss of $74 million.

Beyond, Inc. acquired another bankrupt brand, Zulily, for $4.5 million in cash in March. Look for that retailer of women’s and children’s apparel to relaunch this fall, having ceased operations in December.

Beyond, Inc.’s stock price on August 22 was $11.02, a five-year low.