Feel the Boot

I recently talked to serial entrepreneur Johann Moonesinghe about his experiences as a founder and investor. He was one of the first people in the country to try equity crowdfunding, focused on restaurants.He actively invests in and advises tech startups through TechStars and directly.We talked about how the COVID crisis impacted restaurants and other startups, and the common elements among those that are surviving.He shared his experience as a gay minority founder and the importance of mutual community support.Finally, we dove into his process in choosing what companies he wants to invest in and his advice to new entrepreneurs.Get the podcast here https://ftb.bz/podcastJohann recommended:StartOut Growth Lab - LGBTQ+ focused accelerator https://startout.org/growth-lab/TechStars Accelerator https://TechStars.comLinkedIn (don’t forget the obvious tools) https://LinkedIn.com

In my recent interview with Joy Hermsen, we talked about a wide variety of issues and ideas critical to entrepreneurs, including finding mentors, startup survival strategies, how training for triathlons relates to entrepreneurship, and getting or giving frank feedback.Joy’s experience in business and from teaching entrepreneurship and leadership shines through in this conversation.Bio:Joy Hermsen is an educator, connector and strategist who loves to help aspiring doers do. Of all the roles she has had over the years, teaching Entrepreneurship and Leadership is her favorite, allowing her to draw on her experiences as a founder, intrapreneur and “Chief Activator” in organizations large and small. As Statewide Director of Retail/Hospitality/Tourism for Economic/Workforce Development at the CA Community Colleges, she connects industry to students and campuses across the state. By asking direct questions such as “Why not?” and “What are you waiting for?” Joy has managed to annoy some and inspire most.Links:Blog https://ftb.bz/41BPodcast https://ftb.bz/podcastWebsite https://FeelTheBoot.comFeel the Boot Founder’s Alliance https://ftb.bz/allianceJoy’s recommended resources:Sacramento Entrepreneurship Academy https://www.sealink.org/Marketplace https://www.marketplace.org/Kaufman Foundation https://www.kauffman.org/

Intelligence, skill, and hard work are necessary for your startup to succeed, but they are often not enough. In my experience, you need to be lucky too. In this blog, I will share some of my experiences with creating luck and opportunity to help you make and exploit them yourself.The corpses of companies with good ideas and execution litter the entrepreneurial landscape. I know that many of my competitors were at least as smart and tireless as me. I also know just how many times luck played a pivotal role in our survival. We had many “by the skin of our teeth” escapes and miraculous opportunities that dropped in our laps. Some of these are “only over a beer” stories. But, I will tell you a few that will illustrate how you can take control of your luck to a degree. Let’s talk about how you can make your luck and exploit it when it happens.Watch the video: https://ftb.bz/40VRead the blog: https://ftb.bz/40B

I recently had the chance to talk with Michele Chaboudy.She is an experienced senior executive, serial entrepreneur, consultant, and angel investor.Michele is vice-chair of the north bay angels and teaches innovation at Santa Rosa Junior College.Her background and experience are wildly diverse giving her insights broad applicability.In this interview, she shares tons of useful advice for any founder or CEO.In the course of our conversation, we talked about:how many young entrepreneurs misunderstand networking. It is not handing out business cards over drinks and hors d'oeuvres. It can happen every day, all the time.her favorite analogy, taken from her experience racing motorcycles. You need to be looking at least two turns ahead because you go where you look.her process for evaluation companies as an investor, and what matters most to her.how she teaches founders to develop a strategic mindsetwhat entrepreneurs need to know about researching their intended customersFeel the Boot Founder’s Alliance: https://ftb.bz/allianceMichele’s startup consulting website: https://macabbey.com/blogMichele’s suggested resources for founders and entrepreneurs:https://helloalice.org---co founded by Elizabeth Gore, who was also interviewed on Feel the Boot.Simon Sinek— https://simonsinek.com/ particularly his “Start with Why” (book) and any of his speeches.Scott Berkun— https://scottberkun.com/ - “Dance of the Possible” book and “Saving My Creative Soul” (video). All of his books and talks are excellent.Malcolm Gladwell, recommend all of his books including his latest, Talking to Strangers.Tina Seelig— http://www.tinaseelig.com/ - Stanford prof in engineering dept teaching innovation. Favorite book: Ingenius. Recommend any of her books and Ted Talks.Jason Calacanis— https://thisweekinstartups.com/ Interviews Start-up Founders/CEO’s. Recommend his book on angel investing for tech start-ups.Range by David Epstein. Why Generalists Triumph in a Specialized World. —The worst thing you can do is ask a kid what he or she wants to be when they grow up. Try to keep all your options open and don’t worry about starting “late” in a pursuit.Lean Impact—How to innovate for radically greater social good by Ann Mei Chang. Takes the Lean Start-up concept and applies it to non-profits.

When you pitch investors, your audience will only remember a couple of ideas. Your job is to make sure they are your biggest strengths. In this blog, I will help you identify the aspects of your company that will wow investors.I talked in previous blogs about why you need to highlight the most important strengths of your business in any presentation, particularly in pitches. If you need help creating the pitch, check out my complete pitch building process, check out this blog.How do you decide which aspects of your startup will be the most important to this audience of potential investors? First, you need to get inside their heads. Try to understand what about your business will impress them. If you have not watched it, it might help to go back and revisit my blog on the nine things angels want to see in an investment pitchI think that some real-world examples might be the most effective way to illustrate the kind of strengths that impress investors. In this blog, I will consider four companies I know well and the characteristics that made them stand out to me.One thing that may surprise you is that none of these are about the technology or cool solution itself. Obviously, the solution needs to be valuable and desired, but there are a lot of companies that meet that standard. Most often, the startup’s best aspect is something outstanding about the company or business model.One – Pet wearables platformIf you follow our interviews, you may already know the company I am talking about. They make a smart modular pet collar with an associated smartphone app. The app has a marketplace and supports other kinds of third-party integrations.While they have gone through a few pivots, both in their products and in their messaging. I think they have nailed their key ideas.This is a Platform, not a ProductThe marketplace for smart pet devices is crowded, and many of them are having difficulty standing out. The company avoids that problem by positioning itself as a platform. They integrate deeply into the whole pet ecosystem and the lives of the owners.The platform also provides multiple potential streams of revenue and partners that can act as sales channels: pet food, toys, medicine, vets, groomers, walkers, boarding, training, and many more. Also, the integrated platform is more sticky than a simple device. Switching to a different collar would disrupt many other relationships.Additionally, they have active contracts with partners that are paying the company to develop integrations and are committing to help with marketing. They are in mature discussions with several more possible partners with different offerings.This shows people that the idea is not some fantasy, but is real and works.What I remember from their pitch: a platform, not just a device, with proven traction.Two – Virtual group sports watchingThis company created an app that allowed friends from college to continue to watch sports together virtually even after they scattered to the corners of the globe.This company is inherently viralYou can’t watch sports with friends by yourself (obviously). Users have to recruit their friends to the platform. Because we don’t all have the same friends, that person would invite a different set of friends for other events. This exponential growth would expand the userbase automatically.The company only needed strong execution to generate the effect. The company was inherently viral.In addition to growth, the network effects in the business could exclude latecomers to the market. Once all your friends are on a platform, you don’t want to try to get them to move to a new one. If even one of your friends does not want to switch, the group will default back to the original one.The pitch focused on the inherent virality of the business and how it created both growth and defense.Three - Medical devicesI have seen several medical device companies that share the same strength. This is not a problem. Highlight your real strengths rather than something unique but less impactful. Their solutions were all very different, but their strengths happened to be the same.This team will winThese companies all had effective products, solving big problems, in large markets. But that was not the grabber. What made them a compelling investment was the team.The founders had worked together on previous successful medical startups. They have a track record of success. They know the space, the opportunities, and the traps. They already have relationships with manufacturers, doctors, insurers, the FDA, and so forth. They can talk about precisely and confidently about how they will bring the solution to market.With a team like that, there are few unknowns and a high probability of success. That is music to the ears of an investor.All the companies made a point of focusing on the obligatory team slide.Four – Water-saving next-generation irrigationThis company developed an innovative lawn irrigation technology that saves water and reduces installation labor costs. They are reaching their market through landscaping companies who sell and install the systems for end consumers or institutions.A Win-Win-Win alignment of interestsThe key idea, and what pushed me over the line to become an investor, was how the company ensures that all parties are highly motivated.The landscapers love it because installing this system takes a fraction of the time/labor as a conventional one, while the hardware costs are comparable. But, they charge the same price, so their profits go way up.The customers love it because, for the same price, they save a ton of money on water. They also feel good about helping to conserve a scarce resource.Recruiting new landscaping contractors is easy, and each one then drives new sales. Win, Win, Win.Some companies have a murky path to market. Their deck made it crystal clear why this would get traction and take off.Of course, there is much more to say about each of these businesses. All of their pitches hit all the required points. At the end of the presentations, I felt comfortable with the companies. They had addressed all my concerns. But, beyond that general feeling, the things I still remembered days later were these key points, which was the point. If you can identify and emphasize the best aspects of your business, as they did, you will have a big leg up on most of your competition.The same concept applies to marketing, just with different points. Your customers won’t care about the same things that motivate investors. The smart collar company does not talk about platforms in its advertising; it talks about protecting the health and safety of fur-babies. The medical device companies talk about the health and cost benefits of their solutions. The irrigation company talks about improved profits and sales to landscapers and about saving money, saving water, and saving the planet to the customers.Hopefully, those examples will be helpful with finding your key strengths. Many founders have a hard time with this exercise because they are too close to the business. They understand all the details and subtleties and may think the big picture is too obvious to state. If you are having trouble, find an outside advisor or peer to help you get the perspective you need.Let me know if this helped clarify how to find those key strengths or whether I need to take another crack at it. I would love to hear about the aspects you identified either in the comments or over in the Founders Alliance group.

I recently had a chance to interview Lisa Tamayo, serial entrepreneur, angel investor, CEO/Co-founder of Scollar, and my close friend.We talked about their pivot from product to platform, and she shared hard-won experience about the startup process that will be invaluable to any new founder.Video: https://ftb.bz/37VBlog: https://ftb.bz/37V

This is the second video exploring a process I developed for helping you find the optimum direction and strategy for your business. In part 1, you captured a wide range of possible concepts, then systematically narrowed them down to just the best few. If you have not already read it, I suggest you go back to part 1 before reading this. https://ftb.bz/35VIn this part, you will dig deeper into your best business ideas to crown an eventual winner.You can also read this as a blog. Part one at https://ftb.bz/35B or this part at https://ftb.bz/36BDigging deeper on your top options:You narrowed your options down to just a few top options using a quick process based mainly on your experience and intuition. Now you can spend some time exploring only the best strategies in more detail. The fundamental question is, can you win with any of these business directions?Read as a blog: https://ftb.bz/36BWatch as a video: https://ftb.bz/36V

If you need to choose a problem to solve, identify their customers, and settle on the solution for your startup to bring to market, this video is for you.This tool can also be useful for thinking about your pivot options if your current direction is failing.You can read this as a blog at https://ftb.bz/35BThis video explains the first part of the process where you develop a large number of possible business directions, then systematically narrow it down to a few best candidates. In part 2, you will learn how to drill down and analyze those finalists to pick the one business model most likely to succeed.Download the worksheet for this process here: https://ftb.bz/35-business-plan-worksheetAs you work through this process, you will uncover your optimum business direction.For each potential path, you will consider the following criteria:· What is the need, pain, or unfulfilled desire?· Who needs that, and how would they use it?· How many people fit that description, and how urgent is their need?· Your proposed solution· Why that solution is better than competitors, alternatives, or workaroundsYou should be able to do this initial exercise in a day. After that, you will need to do some more research and conduct tests to see if your guesses and assumptions are right. Using this worksheet is a navel-gazing activity, but you can’t navel-gaze all the way to your final destination.One thing I did not include in the worksheet is your passion. Because startups are all-consuming, make sure whatever direction you consider is something you would love to spend all your time doing for a long time. Don’t write down an option if you are not willing to do that thing at maximum intensity for years.Digging deeper on your top optionsPart 2 of this video covers how to look more closely at your top contenders and pick the one strategy you want to pursue for your business.A work in progressI am using this tool with some of my portfolio companies, but it is not as mature as most of my other advice and methodologies. If you try it, please give me feedback about what worked and what you think needs to be adjusted. Thanks!

I recently had a chance to talk with Iris Fujiura, Chapter Lead of the Silicon Valley chapter of Golden Seeds, a national network of angel investment groups focused on woman-run startups. Prior to that, she was an engineer, and eventually an executive, working on rockets and launch systems.Video version: https://ftb.bz/34VBlog version: https://ftb.bz/34BShe provided great insight into angel investor priorities, and what makes for a successful funding pitch. We also discussed the particular challenges facing female entrepreneurs.Iris recommended the Female Founders Alliance https://femalefounders.org/ as a particularly useful resource.

I answer more questions and provide more coaching about investor pitches than anything else. Once you decide that you need investment to grow your company, your task as a founder is to convince investors to give it to you. The first step in that process is a pitch, and getting it right is essential to the future of your business. In this blog, I will share with you my five-step process for building a killer pitch.Read the blog: https://ftb.bz/33B Watch the video: https://ftb.bz/33VThese steps are a process, not a recipe. I don’t have template slides where you just fill in the blanks because we are not playing Mad Libs. Your pitch needs to be unique and crafted to highlight your company’s strengths and relative advantages.As you create your deck consider its purpose and your objective. It exists to get you the next meeting, nothing more. If you generate enough interest and excitement to move forward with due diligence, you have succeeded.The five steps are:· Gather – capture all the information investors might want to learn· Focus – Zero in on the key elements· Organize – Layout the flow of your presentation· Build – Create the actual slides· Polish – Refine your presentation until it singsGatherStart by pulling together all the information that your deck will probably require.Jot down your answer to each of the following questions. Some may require time, research, and analysis to answer well. Here is a link to a worksheet with all five steps and these questions: https://ftb.bz/pitchdeck-worksheet1. What is the business?a. What problem are you solving?b. How are you solving it?2. How will you growa. Go to market plan3. What is special about it?a. Any secret sauce, unfair advantage, etc.4. Why is this defensible?a. Moat, defensible IP, network effects, etc.5. Who is the customer?a. Why do they need the problem solved?6. Competitiona. Why much better?b. Why not just use an existing solution?7. Business modela. How do you make money?b. If not now, eventually.c. Key economics8. Financial projections & roadmapa. Can you survive?b. When do you need more investment?9. Why now?a. Market trends?b. New technologies?c. New opportunities?d. New problems?10. Why this team?a. If there are gaps, own it and answer how you will fill them.11. Current statusa. What have you accomplished so far?b. What exists, and at what level of maturity?c. Customers and traction?12. What is the deal?a. Amountb. Structure – equity, note, SAFE, etc.c. Valuation if setd. Terms – discount, interest, preference, etc.If you don’t have satisfying answers to these questions, you might not be ready to pitch. It would be better to spend time researching, testing, and refining the business rather than pushing forward with developing your deck. With most investors, you only get one bite at the apple. Don’t waste it by going in half-assed.FocusNow that you have all the information that might go into your deck, you need to bring some focus to your presentation. Try to highlight what your audience needs to hear, not what you like to talk about. I wrote a blog on the nine things angels want to see in your pitch: https://ftb.bz/31BTry to keep your explanations at a high level. If the audience wants to know more, they can ask questions or dig deeper in due diligence. Don’t get into the technical details of your product unless it is absolutely required. On the other hand, DO state the obvious. Things about your business or market that are obvious to you may not be to most investors.Thinking of your business as a whole, and referencing the list you made in step 1, what are the best things about your startup? Do you have any business superpowers? What are your particular strengths or aspects that make you stand out? Make a note of that to ensure you highlight it during the pitch.Then, look for a few other things about your company that the audience must understand and remember. Limit yourself to just a few. After a few days, most people only retain 3-5 items from a presentation. Choose yours carefully and make them count.Look for and remove details or trivia that does not need to be in the deck. If the investor does not need to know something to understand your business at a 60,000 ft level, it should go. Every slide, every word, every idea, needs to fight for existence in your pitch. Be brutal in your focus.OrganizeNow you need to pull all those ideas into a coherent structure. A pitch is just a special kind of presentation. For a deeper dive into presentations and presenting in general, check out my hour-long presentation training video: https://ftb.bz/P2VYou won’t be able to get away with creating just one deck. Different contexts require different decks. One size will not fit all. You will frequently need to adjust your deck to fill the amount of time they give you. You should never need to rush or stall to hit your allotted time.You will also need to customize your deck for each audience. If you are addressing a random group of angel investors, you will need to explain some things that are blindingly obvious to you.However, if it is a group of industry experts, they might be insulted by that kind of remedial level information but want to see more details of your solution.Finally, and I have ranted about this in a past blog, create different decks for presenting in-person vs. emailing to be read alone.I want to make a radical suggestion; resist the urge to start using any kind of presentation software at this point. I use 3X5 cards, mind maps, or sticky notes to organize my presentations.The key is making it as easy as possible to reorganize your deck. You need to be able to see everything all at once and shuffle it around with zero effort. For simplicity, I will just talk about my process with cards.Another advantage of jotting just a couple of words on each card is that you can cultivate a Buddhist detachment towards them. You spent no time making them, so it is easy to rip them up and replace or change them. Keep the process as frictionless as possible.Capture on the cards all the information you decided to keep in the presentation and lay them out in what seems like a reasonable order. Mark the headline and key point cards so you can see if they are getting the emphasis you want.The first and last things an audience hears will be the most memorable and carry the greatest impact. If you can, put your headline in one or both of those places. I did a blog on nailing the opening of your pitch here: https://ftb.bz/17BThink about your pitch as a story. Narrative is far more memorable than data, particularly if you invest it with emotion. Is there a way of organizing your presentation so that it tells a story about you or your customers? It could be a story about how you came to found the company or a story about a real or imagined customer. One of my portfolio companies created a children’s picture book to illustrate their product and found it to be incredibly effective in all kinds of contexts. Try to connect all the content in your pitch with a single thread running throughout the presentation.Next, consider the transitions between each concept. Walk through the cards in order and think about what you will say as you advance through them. Does each one follow logically from the one before? Do they build a narrative? Do you make any statements or claims before showing the supporting information or context to understand them? You may need to change the order, add, or remove cards to make things flow smoothlyNow, start practicing the pitch. Do it right from the cards while everything is still easy to change. Present or read (depending on whether it is a delivered or emailed deck) all the way through, making notes and changes as you go. Continue to feel for those awkward transition points. Look for places where the pace drags. Notice if you are spending too much time on less important things. Check whether the key points stand out and are positioned for maximum impact.Fix the problems you found, then do it again and again until it feels good.BuildIn many ways, this is the easy part. You know all the slides that will be in the deck, why they are there, and what you will say about them. Now, go create those slides. I usually start by making a blank slide with the tiny bit of text that was on each card.From there, I start zeroing in on the exact content for the slide, of which there should not be much. Slides must be clean and uncluttered, even for read-alone decks. For delivered presentations, the audience must be able to read it from across the room in a couple of seconds. When someone is reading a slide, they are not hearing what you are saying. Your spoken words carry much more weight than the text on the slide.In a presentation, slides only exist to support and enhance your words. They need not, and should not, stand alone. Steve Jobs was a master of this. When he introduced the new MacBook Air, he talked about how small it was, not with numbers but by pulling it out of a mailing envelope.And the computer on an envelope was all you saw on the screen behind him. Focusing on and reinforcing that one concept made it memorable. Every article written on the launch used that example.If you have enough artistic talent to make the deck look fantastic, great, get to work!If not, mockup the slides, create rough diagrams, and find appropriate graphics or images. Then hand it off to a designer who can make it look professional. With all the content planned out and prepared, it should not cost much to get it looking fabulous.PolishNow is the time to start polishing your pitch to a fine edge. If you will be delivering the pitch verbally, whether in person, video conference, or recording, make sure you know the content inside and out. Don’t memorize the words you will say, but rather the message you want to deliver. Internalize the point and purpose of every slide. A memorized presentation often feel awkward, wooden, and over-rehearsed. The only exception is the opening, which can lead to stumbles, so knowing the first few sentences word for word can help. Practice until you can consistently deliver the pitch, in your improvised words, within the time limit.Next, get feedback from as many people as you can. Ideally, use people who are not familiar with your company, so they better reflect the mental state of your real audience. Find people who are willing to hurt your feelings. You want them to tell you, in great detail, why your baby is ugly. Embrace the power of frank feedback. For read-alone decks, let them read it without you in the room. For presentation, present just like you would in the real meeting.Afterward, don’t just ask what they thought about your pitch, pose specific questions.· Where did they get confused?· Where did they lose interest?· Did the pitch make them excited about the business opportunity?· For a presentation, how was your delivery in terms of energy, eye contact, body language, and vocal tone, and filler words?· Did the visuals and layout of the slides help with their understanding?· Ask them to explain your business back to you. Did they understand the key points you wanted them to?· Watch your audiences for clues as to where they are more interested, dubious, or checked out.Lather – Rinse – Repeat. Keep improving the deck and showing it to new audiences. This process never stops. No pitch is perfect, you can always find ways to improve it, and your company will be continually evolving, requiring you to adapt your content.PitchPitching is not your core business, so it seems unfair that your success or failure could depend on something so unrelated.But it does.Your pitch needs to be amazing because the competition is intense. I see lots of good companies fail to raise funds because of weak presentations. As hard and wasteful as it can sometimes seem, take the time and invest the effort to make yours sing. You may even find that this process helps clarify your thinking about the business.If you use this process to build or revise your deck, I would love to take a look. As an incentive, I will give the first ten submissions detailed feedback over a coaching call. Warning, I am one of those people willing to tell you that your baby is ugly, sometimes in gory detail.