As the startup grows it will add new entries to the cap table including new hires, option pools, advisors, as well as new investors. Here’s a list of potential changes to the cap table to watch for: New hires and options pools must be added. Employees who leave before all options are vested will have […]

Cap Table stands for Capitalization Table and tracks the equity ownership in the company. This includes the number of shares each one owns and what percentage of the company it represents. It also lists the total number of shares issued as well as the number of authorized shares by the board. Your number of shares […]

An advisory board is a group of three to five people who provide advice on how to grow your startup. They bring experience, contacts, and domain expertise. Advisory boards help the company grow and succeed. In recruiting for your advisory board, consider the following: Recruit diverse skills, networks, and experiences so they don’t overlap. Use […]

Once you’ve found an advisor you want to bring on board, consider the compensation. It’s important to pay the advisor something for their time and experience. Real work requires real pay. Not all advisors bring the same level of support to the startup. Also, consider that equity increases in value as the company grows. Later-stage […]

In recruiting an advisor, check to see if they have what it takes to be a good one: Have they been through the wringer?   Those who have been tested, such as nearing bankruptcy or going bankrupt will have a deeper understanding of the challenges in running a startup. Will their work with you put them […]

Here are some warning signs you may be talking to the wrong advisor: Their primary business-building experience came two tech generations ago. They have business experience but only in one area such as sales or marketing. They can relate their experience but have difficulty understanding your situation. They have a strong ego and center most […]

Once you decide you need an advisor, you’ll need to find and select one. Here are some key points to consider: Start with your network and expand out from there. Hold several conversations with the candidate advisor before making a decision. If you need to raise awareness for your startup, consider a thought leader in […]

In working with an advisor for your startup, look for these characteristics: – The advisor has first-hand experience in the industry, running a business, closing sales, and more. – They listen and can relate your problems to actionable solutions. – They have been through the same challenges and experiences as you are going through. – […]

In choosing a startup to advise, it’s important to find the right fit. Here are some key points to make sure you are a good advisor to the startup. Spend time with the startup to really understand if you can add value and if they are ready for an advisor. Make sure you communicate well […]

Advisors take many roles in their work with startups. You can use advisors to fill gaps in the early stage of the startup. Some advisors provide support as informal advisors.  There’s no set goals, meetings, or formal advisor agreement. This is the most common way startups work with advisors. Those advisors signed up with an […]

There are several types of advisors you can choose to help your startup. Here’s a list to consider: The Brand Name – This type of advisor offers their name to your company.   This can be helpful to attract investors, employees, and customers.  They typically bring some value in the form of advice, but it’s primarily […]

Good advisors bring good value to your startup. Great advisors bring great value. Spend time identifying the right advisor. In recruiting an advisor, pose specific questions and gauge the response. How does it rank compared to feedback from other sources? It should be the best or near the best of responses. If they advise other […]

As an investor in a startup, you may want to provide additional value and sign up as an advisor. Here are some key points to consider: – Choose startups that you can help. – Make clear the work you plan to do such as introductions, networking, advising on the domain, or just sharing business experience. […]

Advisors can be very helpful to startup founders.  Here are steps to consider in selecting an advisor: 1. Check your company needs for the coming two years and determine what is missing. 2. Look for advisors who add value to the team by bringing the necessary skills and experience the team doesn’t already have. 3. […]

Just as you have an ideal customer profile, so you should have an ideal advisor profile. Start with your industry and growth strategy and look for founders who have experience in the same. Look for someone who has already gone through what you are going through now. Start with those who are local and reach […]

Advisors can help startups achieve higher growth, avoid problems along the way, and give the founder confidence. Here are some key points in choosing an advisor for your startup: – Avoid the “dabbler”. These advisors want to dabble with startups but don’t have any substantial experience to share. – Avoid “Yes” men. These advisors confirm […]

Advisors can be helpful to your startup. Here are some key points to consider to determine if you need one: – If you haven’t run a startup before you’ll most likely need an advisor. – If you plan to raise funding, you’ll find advisors add gravitas to the team as well as potential contacts. – […]

The Convertible Note is a commonly used investment structure for funding startups. It’s a short-term debt instrument that converts into equity later. If the issuer wants a debt instrument without conversion to equity, a promissory note would be a better option. With a Convertible Note, the investor receives accruing interest while holding the note. It […]

Equity is used for investment purposes to give the investor an ownership stake in the company. To calculate your ownership percentage you take the number of shares you are purchasing and divide it by the total number of outstanding shares. Another way to calculate your ownership is to use the pre-money-plus-investment-equal-post-money valuation equation. Each share […]

SAFE stands for Simple Agreement for Future Equity. SAFE notes were created to provide a convertible note-like structure for startup funding but without interest rates or maturity dates.  The SAFE note operates like a warrant which gives the investor the right to buy shares in a future-priced round. SAFEs are similar to convertible notes as […]

The traditional method of going public with an IPO is being challenged by a new model called a Direct Listing.   The IPO is typically run by an investment bank which hypes the new offering to investors to create a market. This oversubscription creates artificial demand for the stock.   After launching the IPO, the issuing company’s […]

In raising funding or selling your business you may consider using an investment banker.  Here are some key points to consider in making the decision: They can build out the dataroom and do the appropriate research of competitors and comps.  An investment banker can create competition for your acquisition thus raising the buyout value.  Fees […]

In negotiating the exit with an acquirer, you’ll need to know the following: 1. Key metrics about your business, both those that show the company in a positive light as well as a negative one. 2. The total addressable market for your company. 3. The top three opportunities your company can attack. 4. The company’s […]

Most startups are launched with the idea of selling the business for a substantial gain in five to seven years. Many companies reach that stage and find they can’t sell the business, at least not for the price they want. Here are some options: – Reduce your burn rate to zero and keep running the […]

In setting the exit, most investors look to maximize the exit value. It’s important to remember that the metric investors use, IRR or Internal Rate of Return, has a time component to it. The faster the exit, the higher the IRR. As an investor, consider pursuing the highest IRR and not just the biggest dollar […]

Most exits come from another company buying the startup.  It takes six months to a year to complete a buyout. Delays often come from the startup not being prepared or ready for the M&A process. Also, setting a valuation and final terms can take substantial time for research and negotiations. To shorten the time consider […]

In selling a business there are two types of buyers: strategic buyers and financial buyers. Strategic buyers look for companies that can enhance their current business. Financial buyers look for companies that generate cash. Their motivations and careabouts are different. The strategic buyer will look to see how closely the acquisition is to the buyer’s […]

Startups should start planning for an exit after they achieve product-market fit.  Here are some key points to consider when planning your approach to an acquirer: – What are the key metrics the acquirer will look for? – What are the company’s metrics and how do they currently look? – How big is the market […]

There are several ways to exit a business. You can sell the business to another company or investor. This provides liquidity to the owners.    The downside is, it’s not clear what happens to the employees and the direction of the company. You can develop an employee stock ownership plan. This transfers ownership to the employees […]

Most startup exits come through acquisition by another company.  In planning for an exit, you need to develop a strategic plan that prepares your business for the target acquirer. Here are some key steps: Identify the target acquirer and make contact with the CEO and VPs of the company to discuss a potential acquisition in […]

Investors should gain alignment with the startup about the exit before making the investment. This includes the size and timing of the exit. There needs to be some clear thinking and research about who will buy the company and how much they will pay.   The investors and the startup need to work together to achieve […]

There are several options for selling your business. Here are some of them: Strategic – This is a buyer that buys your business as it provides strategic value for their company. Financial  – This buyer looks solely at the financials, in particular, the cash flow, and buys the company without consideration to the strategic implications […]

Even in the early days of the startup, the CEO must keep in mind the exit.  The investors funded with the anticipation of a return. While the vision of an exit may seem like a distant future, the decisions taken at the beginning often impact the exit at the end. Selection of business model and […]

Startup investors look for an exit in the 5-7 year range. As a startup, you need to consider the exit from the beginning as the exit strategy can inform your decisions around funding, hiring, and more. Here are several exit options to consider: – Mergers and acquisitions – most companies exit by being bought by […]

Here are some key steps to take in planning the exit for your company: – Understand why you are exiting the business.   – Is this exit going to be seller motivated or buyer motivated? – Explore the options. Consider who would be the best acquirer or which company would be best to merge with. – […]

There are many reasons to exit the business. Here are some key ones to consider: – The company is ready to go IPO. By taking the company public, new ownership comes into place. – The market has changed dramatically putting the future of the business into question. – The business failed and can no longer […]

For every business, there comes a time to sell it. Ask these questions to find if now is the right time to sell your business. Do you still want to run the business? You may want to move on to new projects and opportunities and the current business may no longer be fulfilling. Do you […]

Startups have a high failure rate. What percentage fails? Out of 100 startups/investments: -75 will fail or turn into a lifestyle business within 2 years  -25 will remain on the venture track after 2 years Of those 25: -half will die or turn into a lifestyle business between years 2-4 -15 will remain on the […]

Running a fundraise with investors is similar to running a sales funnel with prospects. You must take the investor through the stages of awareness, interest, desire, and commitment. Here are the steps you need to take: Stage 1: Awareness – identify and contact an initial list of investors. Start with an ideal investor profile. Categorize […]

After you’ve had an introduction and talked with the investor either in person or on the phone, it’s important to follow up with the investor to answer questions, update about progress, and walk through diligence. Investors are not interested in spending time to hear about your forecast, they are looking for updates about your progress […]

In startups, cash is king. It’s the key financial metric to watch. Growth may be going straight up, customer traction may be better than ever, but if cash runs out then it all comes crashing down. Cash management is a daily exercise.   The first step is to understand every inflow and outflow of cash.   Set […]

Platform products facilitate two-sided marketplaces that match buyers to sellers.   The most common metrics used in platform products are buyer/seller metrics, inventory metrics, and transaction metrics. Buyer/seller metrics include the number of buyers and sellers on the platform. Also, the growth of buyers/sellers and the number of repeat buyers/sellers should be measured. For inventory, metrics […]

Many startups use SAFE notes and Convertible Notes for their early-stage investments. So what’s the difference? A convertible note is a debt instrument that converts into equity later upon an event such as raising an equity round or reaching a maturity date. A SAFE is a Simple Agreement for Future Equity which is a warrant […]

Storytelling is a key skill for any startup raising funding. In the early days of a startup, the product and team aren’t fully developed and customers are typically not fully engaged.   The investors look to the founders to understand the potential of the business.   The founder who can articulate a clear vision of the company […]

In seeking a buyer for the company, there are two basic choices: a strategic buyer or a financial buyer.   The strategic buyer is typically a company in your industry that is seeking to acquire technology, teams, a customer base, or brands. They will look at those aspects of your business for a potential fit with […]

After you complete your fundraise and thanked those who helped you, take time to prepare for the next fundraise. Take the investor prospects, the ones who did not invest, and add them to a list to update every 3 to 6 months about your progress.   Investors are often curious about how the business turned out, […]

After the fundraise is complete, wrap up the current raise by doing the following: 1. Thank those investors who helped you, as many of your contacts made introductions, offered advice, and more. 2. Also, thank team members, friends, colleagues, and providers who assisted you.  3. Close up the due diligence box and store it where […]

I’m often asked what return angels and venture capital investors seek in their startup investments. Angels generally seek around a 30% IRR (Internal Rate of Return). That would be 3X their investment in four years. For longer timeframes, angel investors will be looking for a 5X-10X return for a startup investment. The longer it takes […]

Investors calculate their returns using metrics ROI and IRR. So what’s the difference? ROI is the return on investment without respect to time. IRR is the internal rate of return which is the return on investment with respect to time. If I invest $100K and 5 years later I receive a return of $300,000, then […]

I’ve seen CEOs pitch and when asked about their numbers, they defer to a CFO or someone else for the answers. This is not a good look for the CEO. Investors want to know you are on top of it, and knowing your numbers is one indication of it. As a startup, you should know […]

In raising funding, you’ll need to propose a value for the equity in your startup. This is called valuation. One way to determine it is to use the liquidation method. Here’s how it works. The exit value is set to the value of the business at liquidation, which means the value of all assets minus […]

In raising funding, you’ll need to propose a value for the equity in your startup called valuation. One way to set a valuation is to use the 5X your raise method. Here’s how it works. Most investors want to see the valuation for their money coming in at 20%-25% of the post-money valuation. This gives […]

In launching your product you have a choice to either set a high price that gives you a high margin, or a low price yielding a low margin for sales. The high price is harder to sell, but you don’t have to sell as many units to make the business profitable. The low price is […]

In running a startup there will be upturns and downturns. Managing a downturn takes a different approach from the upturns. First, seek advice and guidance from others such as investors, mentors, and CEOs. Don’t delude yourself into thinking it’s better than it is and that it will turn around soon. Acknowledge that it’s a bad […]

In a fundraise, one typically uses the same term sheet throughout the raise. From time to time, investors will demand certain rights and conditions.   If there are no investor representations, then you may be able to do so. For some investors, you may need to vary the terms of the raise and use a different […]

In valuing a startup for an investment, it’s useful to find valuations by looking at similar startups. This technique is referred to as ‘comps’ which stands for comparable. This method looks for companies in the same sector and analyzes both exits and investments to determine the current valuation for the segment. This is often a […]

In negotiating the valuation, the investor can use current market comps or comparables to set the initial price. By looking at companies in the same sector and stage, one can find the range of valuations. From there, the investor can raise the valuation based on the values the startup has built already and lower it […]

As an investor, you can often see warning signs of trouble in small ways before they become full-blown in the startup. Here are some of them: – The CFO quits unexpectedly – The paychecks to employees bounce and it’s called an “accounting error” – Information from the CEO becomes limited and they don’t return phone […]

In running a startup, it’s important to focus on the essentials of the business. In your strategy planning, identify the Must-Dos. The Must-Dos have to get done. Beware of the Nice-to-Haves. If you hear yourself saying “wouldn’t it be nice if we did this?”, it most likely will be taking you away from the essentials. […]

Running a startup is hard work. The team must work long hours and often at low pay. This can wear down the team. The CEO should monitor the employees for burnout. Burnout can be caused by several factors: – Work overload — too much work and too little time to do it leaves employees feeling […]

Startups seek to grow as fast as possible. One of the key barriers to growth is the Sales Learning Curve. This learning curve is a combination of the product, marketing, and sales working together to create customer acquisition and a product-delivery system that achieves scale and can be maintained.  In seed-stage funding, the investor looks […]

In launching your startup, you’ll need to determine which sales channel is best for your business. The sales channel is how you reach prospects and then turn them into customers. Most first-time startup founders envision a channel and then assume that’s the best path. Experienced founders know you must research, test, and analyze the channels […]

Choosing a co-founder is an important step in launching your startup. Consider these points before finalizing your decision: – First, understand what are the businesses’ needs and what skills must be recruited. – In the early stages of the startup, you need a complete team — someone building it and someone selling it.   – Choose […]

In planning your startup, consider the challenge you will have in converting users from their current solution to your solution. Customers don’t move to a new product because it’s 10% better. They move because it’s 10X better. Make sure you are positioning your startup to be competitive in the market. To do so, consider 10Xing […]

Pricing the product or service is a key step in running a startup. There are four pricing strategies to choose from: 1. Premium pricing is a price at the upper end of the scale and is used to attract higher-end users. The profit margins are greater here. 2. Low-cost pricing is a price at the […]

I often see founders begin work on their startup by building out their tech platform. Customers will come later they say. I recommend starting with the customer and have them guide you through to the tech platform you need. In the early days, hire a few people to run the process manually.  As the process […]

Most startups envision a product and then proceed to build out an MVP. After they polish it enough they may show it to a customer.   In some cases, they try and take it all the way to a finished product because they want to show completeness to a customer. A customer should be involved before […]

The Venture Capital method of valuation uses a discounted cash flow combined with a multiples-based valuation.  The valuation takes into account cash flows in a best case, medium case, and worst-case scenario. It then uses an industry multiple to set the anticipated sell price. The cash flows and exit price are discounted giving three valuations […]

The CEO must operate in two modes: managing and leading. As a manager, the CEO must define the strategy, recruit the team, and set goals for the company.  This requires strong organizational skills. As a leader, the CEO must set the vision, motivate the team, and create a culture.  This requires having a vision, caring […]

Companies with a strong culture do better with investors, customers, and employees. Building a company culture is the long game, not a short one. From the beginning, focus on instilling core values into the business. As you recruit new team members, they too will have an impact on the culture. Here are some key points […]

Having a strong company culture helps the startup succeed. Customers and partners are attracted to companies with strong cultures. It guides the employees on what is important. The CEO fosters the company culture. In general, CEOs build cultures they like to work in. It’s important to hire well throughout the life of the company. The […]

An entrepreneur raising funding must demonstrate confidence.   Investors will look for someone who has confidence in their plan, their team, and themselves. Oftentimes entrepreneurs fake confidence and come off looking cocky, which is unfounded confidence. True confidence inspires others and persuades them to support the company. Investors look for this in the founder as he […]

There’s a quantitative side and a qualitative side to due diligence. The quantitative side includes checking the list of documents in the data room to verify the accuracy of those documents.   For example, do the entity filings match what the company said they have? Do the intellectual property documents match what they claim they have? […]

Entrepreneurs are often concerned about the confidentiality of their information.  During the initial engagement with the investor, it’s not common to sign NDAs (non-disclosure agreements) as the investor is still figuring out the basics of your business. At the introductory stage, keep the discussion on the general level. As you go further with the discussion […]

In startup investing, investors take in information from the startup about the product, team, financials, revenue, and more. This information does change rapidly in the startup phase of the business.  One method of assuring the investor the information provided is true and accurate is for the startup to sign a Reps and Warranties contract. This […]

In diligencing a startup, the size of the market is a key question. The larger the market, the greater the growth potential of the startup. There’s rarely a need to pay for research as so much exists on the web. In searching the web, you’ll find research reports giving market sizes, trends, analysis, and more.   […]

How can an investor group make the diligence process manageable?  Here are some steps: – Standardize the diligence process – Break it down into subtasks and define the process for each task – Assign the tasks to team members – Set target dates for completion and have periodic check-ins with each team member  – Focus […]

Tools are important for running a deal-flow process.   You’ll need tools for managing deal flow, running diligence, and tracking the portfolio.   For deal flow, there needs to be an application process for capturing the essential information and pitch deck. Examples include Proseeder, Gust, and there are others. For diligence, you need checklists to share with […]

In early-stage investing, someone needs to take the lead and screen the deals, diligence selected ones, and negotiate the valuation with the chosen ones. In most cases, the lead investor doesn’t want to be the only one in the deal and promotes other investors to join.  This promotion process is called syndication. Most investors are […]

In running a diligence process it’s important to keep track of the progress of team members. Set up frequent follow-up calls to check progress and resolve issues. Follow-up calls should be scheduled and led by the deal lead. A check-in call should take no more than 30 minutes. In the follow-up calls, make sure the […]

Hello, this is Hall T. Martin with the Startup Funding Espresso — your daily shot of startup funding and investing. There are three phases to diligence before funding a startup: 1. Documentation diligence 2. Team diligence 3. Domain diligence For documentation diligence, ask the startup for a list of key documents for diligence. The key […]

In running due diligence it’s important to build a team and bring others into the process.  A deal lead should take care of gathering the initial documents so the team doesn’t stall out waiting on the startup. Assign each team member a task and include the instructions for the task. Make clear that the goal […]

After the diligence is complete and the open questions answered, the team must decide whether or not to invest. It’s important to identify the risks and write them out in the report. The team should articulate an investment thesis that includes the opportunity in the deal such as how big it could become.   The team […]

Startups can raise funding even without a lead investor. In this situation, the startup acts as the lead. Here are three steps to take: First, the startup must present investor-friendly terms and conditions. There should be no push back on the terms. Second, the startup must supply a due diligence package already completed. Consider adding […]

Startups who find an investor expressing interest often stop their fundraise as they believe – or sometimes hope – this will be the one who completes the rest of their raise. I tell entrepreneurs to continue the fundraise effort until the funds are in the bank account. I’ve seen deals blow up on the 1-yard […]

A startup investment goes through a series of stages. It starts with the pitch presentation in which the startup introduces the deal to the investors. Then there’s the first follow-up meeting in which the investors dig into the deal to learn the details. Investors want to think about it and also want to see the […]

I’ve had startups approach me and give me one or two lines about their startup. When I start to ask questions, they say they can’t tell me anything more without signing a Non-Disclosure Agreement or NDA. I often find this puzzling, as investors don’t sign NDAs to find out what the startup business is.   They […]

In running a deal follow-up process, you’ll need to create a diligence report. Here are some key points to consider: – Start with a template that lists the required information. – Include instructions in the original template for the team members to follow. – You may be cycling through many members so you should write […]

To pitch an investor, you’ll need a carefully crafted startup story.  Just any old story won’t do.  Tell the story in your own words as if you’re talking with a friend at a bar. Show how the story is relevant to those in the audience, something everyone can relate to. Keep the story simple.  It […]

There are five key elements to a startup story. Today we’ll talk about the Plot. After you establish the theme, hero, mission, and obstacle, you can start working on your plot. The plot is a series of events that leads to achieving the mission. Plots can be set up in several ways and choosing the […]

There are five key elements to a startup story.    The Mission is the job to be done.  It’s the goal of the hero both now and beyond the story. For your startup story, focus on what the CEO is trying to accomplish and how he plans to solve it. Outline how hard the problem is […]

There are five key elements to a startup story. The hero is the character whose journey the audience cares about the most.  In a startup fundraise story, this is the CEO. Most heroes are trusty and likable.   The audience empathizes with them in some way. Your story should focus on the hero and not just […]

Your story is a critical part of your fundraise pitch. There are five key elements to a startup story.   The first is your theme or purpose. This comes from what inspired your startup. There’s something about the world that you want to change so you started the company to fix it. Next, connect your theme […]

There are five key elements to a startup story. Today we’ll talk about the obstacle. The obstacle stands between the hero and the goal. All good stories have a conflict that must be overcome.   Obstacles could be competitors, lack of knowledge, regulations, and more. The obstacle creates tension which holds the audience’s attention and helps […]

There are three stories every startup should be able to tell to investors.  The first is your origin story which tells why you started the business to begin with and how you got to where you are today.   This story answers the question, “Why are you doing this?” which usually comes from the storyline, “I […]

How does due diligence vary between angels and venture capitalists? At a high level, the diligence is the same between angels and VCs. They both look for a good team, a strong market, and a quality product.  At a detailed level, the angels who come in earlier than many VCs will look at a deal […]

In talking with startups, I find the investor must always probe for the final answer. A single question rarely reveals the full answer. I spoke with a startup recently who said, “We’re raising a million dollars and we have raised half of it already.” On the surface, it sounded like they had $500K invested in […]

After an investor expresses interest in funding your deal, the first question to ask is, “What is your diligence process?”. While most diligence processes follow the same format of document review and analysis with follow-up questions, each investor has their own start time, timeframe of work, and specific documents they look for. It’s best to […]

In raising funding just as in running your business, investors look to see if you own it. Do you own the challenging problems, or do you avoid them? Do you own the core business, or do you delegate it to someone else? Do you abide by the contracts you sign, or do you try and […]

In launching your startup, look for a trigger that indicates when to start a fundraise campaign. Common triggers include: – Closing a lighthouse customer account or achieving a revenue target. – Signing up a new team member or advisor. – Finishing a beta version of your software or an MVP version of your product. – […]