Attacking New Customers
Many companies declare war on their customers, sometimes without realizing it. Customers are sometimes wrong, but too often businesses miss information about new markets, new…
Perspective, from Dot.com to Crypto
In the movie Ratatouille, critic Anton Ego, reacting to “overheated puffery” says he craves “some fresh, clear, well seasoned perspective.” Perspective is often missing in…
Attacking New Markets
My board wants me to expand my highly successful business into a number of somewhat related, but mostly peripheral areas. I am worried I will…
Building a Media Strategy
Our company is creating a new category to sell to large enterprises and we need to build a PR strategy to help our business. Do…
Hurting Angel Investors
I have a small angel fund with a few friends. We are not able to invest more in later rounds in all our best deals,…
Running from Regulation
I am afraid that my industry is going to be regulated soon, as Congress is starting to hold hearings. How can I fight against this?…
Testing with Predators
I need to test my product in the field before I can release it widely, but the companies where I need to test the idea…
Not Ready to Take the Leap
I am not yet ready to leave my executive job to join my friend’s unfunded startup, especially since I am paying for two kids in…
Fraudulent Founder Claims
A former friend is claiming to be a co-founder of my company who had nothing to do with my business or idea. I just told…
Finding Startup Advisors
I am unsure how to build a strong group of advisors for my startup or how to weigh their advice. Do you have any suggestions?…
Surviving Board Dysfunction
My Board of Directors is dysfunctional. We are always in conflict with each other and cannot agree on decisions. Is there anything I can do?…
Disclosing Startup Secrets
My advisor told me not to bother having other companies sign NDAs because they are “worthless,” and not to have our lawyers review outside NDAs…
A Farewell to Startup Business Plans
I was taught that I have to create a full business plan, ideally 50-100 pages, with a fully developed product and strategy before I can…
Advice for a First Time CTO
I am leaving a large company as an IT exec to join a friend’s startup as the startup’s initial CTO. Do you have any advice…
Should I Sell My Business?
Your rollup post was timely. We just received an acquisition offer. We have some other projects we think are higher value and this product is…
Should I Roll Up My Industry?
My largest investor asked to me look at doing a “roll up” strategy in my space, buying out smaller players. Do these strategies make sense?…
The GameStop Dumpster Fire
Do you think the GameStop market surge represents a new chapter in investing, as the masses finally can compete with the big Wall Street funds?…
Competition from Ex-Employees
One of my ex-employees just started a new company to compete with my startup. My lawyer said I could not insert a noncompete in his…
Startup Culture Misfits
I built my early stage startup with a few close friends who come from big company backgrounds. They are brilliant and successful, but are plodding,…
Renegotiating Bad Deals
My co-founder and I gave up 75% to our Series A investor for just $1 million. Now that the company is taking off and needs…
Future of Technology Policy
Innovative entrepreneurship drives the global economy, yet it is under attack. Silicon Valley’s success has drawn the wrath of populist outrage. We were never going…
Giving Back
I am an undergraduate computer science student and was inspired by the recent webinar with Tim Connors when he said we should give some of…
Hiding Information
My co-founder is handling the diligence process with our acquirer and I am not comfortable with how loose he is being with some of the…
A Startup Without Employee Stock
I have worked crazy hours for a tech startup for the last two years, starting as the third employee. I have made sacrifices to make…
Bonus Plans for Startups
We are setting up a bonus plan for my startup and making it cash only, as my employees do not want stock. Do you have…
Avoiding Harsh Pay to Plays
I am looking to raise some money from insiders in a Series A-1 deal to see if we can get traction for a pivot we…
Hold Off On IP Holding Companies?
I have an IP holding company which owns all my patents and licenses them to my startup. I am deep in diligence with a potential…
Founder Deadlock
My co-founder and I each own 50% and we are deadlocked on everything. We have no investors or anyone else involved. What should we do?…
Selling in a Den of Thieves
A large company in our space says they want to acquire my startup and wants to do diligence on us. This company has a reputation…
Don’t Panic
Instead of answering a specific question this week, I wanted to summarize a common discussion I am having lately with many companies: remaining steady in…
Getting Exercised About Stock
I got stock at my startup on Friday, which I am exercising this weekend, but to my understanding nothing can he exercised until funding comes…
Patently Unguaranteed
I am negotiating to buy a small company that will not provide any guarantees that it validly owns the IP I am buying or that…
Actionable Investor Reporting
One of my primary responsibilities is to gather monthly reports on our portfolio companies…. The founding partners are a close group of six serial entrepreneurs…
Second Tier Talent
I finally fired my head of engineering, who was dragging us down. Now, the company is aligned, energetic, flying through development, and, well fun… as…
Helping Each Other in Crisis
We live in a world where selfishness often reigns, so it is worth reflecting one critical factor that makes entrepreneurship work: the everyday willingness of…
Protecting Oneself in Chinese Deals
My company is negotiating a deal with a Chinese company. I hear that it is difficult to enforce contracts in China against Chinese companies. How…
How Hard to Negotiate
How hard should I fight with my potential investor for the best valuation? I am inclined to take the term sheet offered, but my friend…
Must I Incorporate in the U.S.?
My business and team are based in South America. We have no U.S. sales or operations but are looking to raise money from U.S. VCs.…
Spouses and Friends As Co-Founders
I was told by an advisor that I should never start a company with a friend or my husband because no investor will invest. Is…
Keeping Your Head Up During Down Rounds
I am an angel investor in a company that is looking at doing a down round “pay to play.” How can I protect myself from…
Should I Push Back On My VC?
I just got a term sheet for a Series A financing. The VC accepted the valuation I proposed, which was aggressive, but added a 2x…
Don’t Panic Over Franchise Taxes
David, help! Delaware says I owe almost $100,000 in corporation franchise taxes. I just started the company last year and I don’t know what is…
Strategic Investing: Pros and Cons for Startups
One of the startups I am working with is looking at taking money from a strategic investor. What are some of the pros and cons…
Entrepreneurship For All
Silicon Valley has a long history of biases in whose startups get funded… Rich white male tech entrepreneurs who can access the generational wealth of…
Choosing a Board of Directors
I am curious about the best recommendations about how to build a board. My last board, foolishly was a group of well intended friends. However,…
Startups and Customer Feedback
When startups receive (hopefully) lots of customer feedback and suggestions on product improvements/features they wish to add, how do you go about deciding which suggestion/feedback…
Convertible Notes vs. SAFEs
Is a SAFE the same as a convertible when raising funds? Many first time founders typically raise their first few funds either way, so I…