The final topic covered in Winning Angels by Amis and Stevenson focuses on an important concept called harvesting that should be considered by entrepreneurs when starting a business. Harvesting eludes to the various exit opportunities that a business can take whenever the time comes. Of course, an entrepreneur does not need to know exactly how he and investors will exit an industry, but it is something that can be a selling point to potential investors if you have some ideas in place. At the end of the day, investors are ultimately looking to invest their money in opportunities that will yield returns. If an entrepreneur can show investors how his/her idea will provide them with returns on their investment, then he/she shouldn’t have too much trouble raising funds.


Amis and Stevenson highlight seven various exit paths that a business may go through. These paths include a walking harvest, a partial sale, an initial public offering (IPO), a financial sale, a strategic sale, and then two not so ideal options known as Chapter 11 and Chapter 7 which would serve as a last resort in worst case scenarios. Of these options, the strategic sale seems to be the most common and sought-after path. The authors describe a strategic sale as one that involves a buyer who “is typically an industry player that will pay value beyond what the cash flows might suggest.”


I found this final chapter to be extremely interesting because quite honestly, I have not put a lot of thought into exit plans when thinking about business ideas. I typically think about things like the quality of the product/service, who will be the target market, how would you market to this demographic, etc. This book and especially this chapter have opened my eyes to the importance of at least thinking about potential exit strategies even though a business may only be in an idea phase. Investors want to make money on their investments as do most entrepreneurs. Therefore, taking the time to think about the end goal can be extremely beneficial in the development of a business. It almost allows you to somewhat reverse engineer your thinking which may help provide guidance when developing a business plan and strategy.

There are many ways in which an angel investor can support an entrepreneur and his/her business. In their book Winning Angels, Amis and Stevenson break down these various roles as silent investors, reserve force, team member, coach, and controlling investor. These roles are listed in order of least involvement to most involvement. Investors normally decide their level of involvement based on things such as how much have they invested, what kind of support does the entrepreneur need, how much time do they have to give, etc. Their level of involvement may also change as a company develops. Many times, entrepreneurs need more hands-on support during the early stages, and once the business is more developed, then the investors can scale back their involvement and be available when needed.


Based on the quotes provided in this book by experienced angel investors, it seems that most of them prefer to have some level of involvement as opposed to the silent investor route. The silent investor seems to be more for a minority investor who is just looking to trust an entrepreneur in hopes of getting some return on their investment. These investors usually have a lot of other things going on to where they simply don’t have the time or desire to have much involvement. I personally would like my investors to have some level of involvement as an entrepreneur, and if I were an investor, I would also like to have some level of involvement in the company I am investing in. One angel, Steve McGeady, says “I always like to add some value other than simply money. I try to get involved in things where I can help out personally.” I love this quote because it shows that the investor cares about the business and wants to help the entrepreneur in any way he can. It also shows the importance of investing in businesses that you can actually add value to outside of writing a check. Money is helpful, but experience and expertise are just as valuable. Especially if it can help you avoid costly mistakes and potentially save you money.


At the end of the day, developing and running a successful business is a team effort. The more people involved who have experience in the industry at hand and a passion for the product being produced, the higher chance of success. I’ve learned that surrounding yourself with well-connected and like-minded people is a must. A mutual respect among business partners and team members is essential as well.

To negotiate or not to negotiate? The question every investor will face at some point during the process of getting a deal done. There are many aspects to be considered when deciding if and how to negotiate. However, one of the most important things to consider is how will the negotiations affect the relationship between the investor and the entrepreneur. Starting off on the wrong foot could be detrimental to a business opportunity.


Negotiating can be a very emotional process, and therefore, many investors prefer not to risk souring a relationship with an entrepreneur over negotiations. So how do these investors ever strike any deals if they aren’t negotiating? The authors of Winning Angels lay out a few options. One, they let someone else do the negotiations for them. Outsourcing this responsibility to an attorney allows the investor to shift any ill will to the attorney as opposed to coming off as greedy. Another option is they leave it up to the entrepreneur. If the entrepreneur proposes a fair deal, then they accept. If the investor doesn’t like the proposed deal, they simply decline the opportunity and move on. A third option is the investor doesn’t care much about the financial aspect at this early stage time. They will accept any reasonable terms presented by the entrepreneur because they want the entrepreneur to feel good and remain motivated to win. Sometimes the investor may also wait until later and more significant investment rounds to negotiate terms. Although it seems crazy to invest money and not negotiate terms, all of these reasons help to justify those decisions.


On the other hand, some investors view negotiating as very important because it is an opportunity to further evaluate the personality, characteristics and values of those you may be going into business with. You are not going to want to go into business with an entrepreneur who is more focused on being greedy and striking the best deal for themselves. And same goes for the entrepreneur when deciding whether an investor is the right partner or not. Negotiations can bring out the true colors of individuals so it can certainly be used as a vetting tool. You also don’t want to go into business with someone who can’t handle a little pressure and find a way to problem solve without getting their feelings hurt.


At the end of the day, there are multiple ways to go about the negotiation phase of sealing a deal. If all parties go into the process with a fair and realistic bargaining range, then it seems likely that a fair deal can eventually be made. And sometimes the best deals are the ones that aren’t done. Not every potential opportunity has to be carried out. Knowing if and when to walk away from the negotiating table is an essential skill to have.

This week’s reading of Winning Angels by Amis and Stevenson focused on the topic of structuring, specifically as it pertains to investment deal structure. This is certainly not a topic in which I have a lot of experience or knowledge; however, I did find it interesting as it is obviously a very important aspect of either investing in a company or finding investors as an entrepreneur. The three structures discussed in this book include common stock, preferred convertible with various terms and convertible note with various terms.


The common stock structure seems to be the least structured of the three. It generally involves a little more trust in the entrepreneur and partners. The other two have more terms and offer more protection to the investor, but they can also sometimes be complicated and sour relationships between investor and entrepreneur. In a perfect world, it would be nice and simple to be able to trust everyone you are going into business with so that everyone benefits in a fair and equitable way. Unfortunately, not everyone can be trusted and when it comes to investing large amounts of money, it seems reasonable to want to have some terms set in place to protect the investment.


While I have never been in a position to be an angel investor to an upcoming company, I have had a recent experience of exploring the opportunity to invest/buy-in to the ownership of a business. As someone who has never been in that position before, I made sure to reach out to people who could provide me some insight and guidance into things to be looking for while doing my research and deciding if it is a worthwhile investment. I talked to other SMEs in the industry, lawyers, and CPAs. I am extremely grateful that I did because they all helped me to come to the realization that given all of the circumstances, what was being asked for would most likely not be a good investment for me at this time. The point I want to get across from my very small experience is that having a strong network can be vitally beneficial when it comes to dealing with aspects of business that you may not have much experience with. I not only utilized preexisting connections, but I also branched out and made new ones through this process. While things did not work out how I originally hoped or envisioned, I certainly learned a lot.

From an outsider’s perspective, I have always found the process of valuing to be fascinating. I have always enjoyed watching shows like Shark Tank where you have investors running through various calculations to create an offer, and you have entrepreneurs showcasing and defending the value of their company in hopes of finding a partnership at a fair price.


I recently went through a valuation process myself as I have been trying to determine whether or not to buy in to a local gym and become part owner. While I won’t share the details of this deal for confidentiality reasons, I still wanted to share my experience compared to some of the strategies brought up in the book Winning Angels by Davis Amis and Howard Stevenson. Luckily, I have made some connections and have had some qualified and experienced people advising me along this process. They helped me to understand what questions I needed to be asking and what information I needed to be looking at. Most of which consisted looking at various financial statements as well as determining exactly how the current owners viewed the future direction of the business. Ultimately, after going through some negotiations, I made the gut decision not to invest in ownership of this business at this time. Given the industry, it seems to make more sense for me to save that capital and invest in my own business and make it exactly what I want.


The chapter on valuing in Winning Angels provides various methods for calculating valuations and determining whether the numbers support a good deal or a bad one. Most of the methods seem to support early stage valuations in the $2-10 million range for a typical angel investment opportunity. While numbers are obviously very important in deciding to invest or not, the authors of the book also point out that the numbers aren’t always the deciding factor. I really liked their splurge on “the feel good factor.” Just because numbers seem to make sense, doesn’t mean that an investor feels great about the entrepreneur or the industry in which the business exists. On the flip side, some investors will make what some would consider bad/higher risk deals just because they believe in the entrepreneur and they want to be in good standing with the entrepreneur for future opportunities as well. What I really like about this topic though is that it tells you to trust your gut. Human instincts are an incredible thing, and I feel as though I have trusted my gut through my recent experience leading me to make the right decision.

This week’s blog post focuses on the importance of evaluating business opportunities as it relates to angel investing. When it comes to investing large sums of money in an early-stage company, doing your homework as a potential investor is very important. In the book Winning Angels, the authors discuss an evaluation framework developed by William Sahlman and Howard Stevenson at Harvard Business School. The elements of this framework consist of the people, the business opportunity, the context, and the deal. These are the key elements that should be taken into consideration when evaluating an investment opportunity.


For this post, I want to focus on the people aspect because it really put an emphasis on the entrepreneur. At this stage in my life, I am focused on entrepreneurship and this topic really helped me understand what potential angels may be looking at should I get to the point of needing investors for a business idea. From reading this book and talking to other successful business minds, I have gathered that the entrepreneur and his team are ultimately the most valuable aspect of securing the investment of an angel. General Georges Doriot, the founder of modern-day venture capital, is quoted saying “I will invest with an A-quality man with a B-quality project, but not the other way around.” I love this quote because it makes so much sense. The entrepreneur/inventor is the engine behind any early-stage business. A product is no good if it doesn’t have a powerhouse willing to put in the long hours required to help get the product to market.


So what characteristics do angels look for in an entrepreneur? First and foremost, a good entrepreneur exemplifies perseverance. They will find a way to win and be successful. Other important characteristics include honest, courageous, competitive, resilient, charismatic, and intelligent. Some of these seem pretty obvious and can certainly be faked during a one-off meeting. Therefore, experienced investors will take them time vetting an entrepreneur to make sure they are who they appear to be. They will ask the entrepreneur countless questions. They will reach out to references provided by the entrepreneur to find out more. They will ask around to other people in the related industry to see if they can find any information on the entrepreneur. By the end of it all, there is no hiding what type of person you are and what type of entrepreneur you will be.


In conclusion, the entrepreneur is one of the most important aspects for angel investors to evaluate when considering a potential investment. The extent to which angels are willing to investigate when they are putting large amounts of money on the table is rather considerable. Therefore, as an aspiring entrepreneur, I am further realizing the importance of networking and building the best reputation I can for myself. Researching this topic has only increased my desire to continue to challenge myself to become more knowledgeable. I plan to do so by continuing to be an active part of my master’s program and to pick the brains of other successful business minds as I increase my network.

I never realized how much strategy goes into angel investing until I began reading Winning Angels by David Amis and Howard Stevenson. Obviously, you have to have enough money to be able to contribute to the growth of a start-up company, but I never really thought about how much money do you need to have. This book does a good job of highlighting things to consider when trying to figure out how much capital one has and how much of that capital should be used for investing. Some of the big things to consider include your family, living expenses, and current/future income. Once you know the details of those, then you can start to think about how much of your net worth are you ok with investing with the expectation that you most likely will lose it all and still be able to support yourself and your family. I think this mindset can help entrepreneurs as well when deciding whether or not to start a business and when big financial decisions come into play.


The authors of the book also emphasize the importance of networking when it comes to sourcing potential deals. Sourcing is defined by the authors of Winning Angels as “identifying entrepreneurial projects of merit.” I found it fascinating to read about why it is important to try to invest in multiple start-ups if possible. You would think a conservative approach would involve doing one investment at a time and seeing what happens. However, the authors make the great point that most of these start-ups have a low percentage of providing big return on investment. You increase your chances of success by investing in multiple opportunities with the hopes that one or two of say 20-25 businesses strike gold. Since it is important to find a handful of viable deals to invest in, networking becomes vital for connecting angels to entrepreneurs. Building relationships within the investing world is how you can generate a constant flow of referrals of entrepreneurs looking for investors and building a reputation as a successful and supportive investor is how you increase your chances of entrepreneurs striking deals with you.


I want to end this post by emphasizing the importance of the investor-entrepreneur relationship. I think it is important for both parties to do their research into the other before striking a deal. Going into business with someone you don’t trust or that doesn’t seem to have a similar vision for the future as you is not the way to go even if they have the money you need. Both parties will ultimately lose in that situation. Networking provides a filter to this process if you will. It allows strong entrepreneurs to be referred to like-minded angel investors and vice versa via a trustworthy third party. So moral of the story is, as an investor or an entrepreneur, continue to learn, research, and meet as many people as you can so that everyone can have an increased chance of achieving success.

Below you will find my analysis of 5 outdoor ads used to promote their product, service, or message. I have enjoyed the creativity of all of the ads I have come across myself and that my peers have shared on their blogs. I feel as though pictures, structures, and interactive ads have the potential to be much more effective than TV or radio ads as they require the viewer to stop, think and process the message being portrayed by the advertising company. Making a viewer actively use their brain most likely means that the message at hand will at least temporarily own some real estate in the mind of the viewer. 


“Dash and Burn” (Netflix – Narcos)

Description: This ad campaign features various forms of creative advertisement in order to promote the Netflix series “Narcos.” The series premiered in 2015 and wrapped up in 2017. One of the ads takes up the space on the side of a bus stop. It is a thin glass case filled with stacks of fake currency. The message on the glass reads “Drug kingpin Pablo Escobar once burned $2,000,000 to keep his family warm.” The glass looks like it has been broken in to and the fake money looks like it has been slightly burned just to provide more theatrics to the ad.

A second ad used in this campaign involved the bottom of security trays in airports where travelers would place their personal items to be scanned. The ads portrayed the items that Pablo Escobar would have been traveling with as well as the items an FBI agent would be traveling with while pursuing the arrest of Pablo Escobar.

Objectives: Both ads intend to let the audience know that all episodes of Narcos can be streamed on Netflix. They also utilize some eye catching and intriguing works of art to give the viewers an idea of what to expect from the show. The goal is to make viewers curious as to what is going on and to almost make them feel they are a part of the show for a split second. The ads are strategically placed in areas where people are traveling (bus and plane) and may be looking for something to pass the time during their trip.

Target Market: Young adults and adults who may be looking for their next TV show to binge watch or looking for something to help them pass their time when traveling. It is especially geared towards those who enjoy violent filled, drug related drama series.

Desired Actions: Log-in or subscribe to Netflix and watch the original series, Narcos.

Value Proposition: The value proposition of watching this show is that you will be entertained and educated on stories surrounding drug kingpins during the 80s. Also, every show can be streamed on Netflix so you can watch the entire series with no interruptions.


“Delicious Going Down” (Maker’s Mark)

Description: This is a large 3D model of a Marker’s Mark bottle placed above the street level entrance to a local metro system. The bottle is tilted and pouring bourbon down towards the metro. The tagline of the ad reads “Delicious going down.”

Objectives: The objective of the ad is to let viewers know that Maker’s Mark is a smooth tasting bourbon whiskey that they need to try. It also uses some humor by combining their primary message with the analogy of people taking the escalator down to the metro.

Target Market: Adults 21 years and older who enjoy drinking bourbon.

Desired Actions: Go buy Maker’s Mark because it is delicious and smooth tasting.

Value Proposition: This bourbon is enjoyable and won’t burn as back as bad as other brands of bourbon.


(Nationwide Insurance)

Description: At first glance, this appears to be a paint ad as there are pictures of paint buckets on the side of the building. One of the lime green paint buckets is on its side and spilling paint down the side of the building and into the parking lot. The paint even covers a few cars in the lot. Off to the right side of the ad is the Nationwide Insurance logo along with their tagline “life comes at you fast.” The combination of humor and disaster provokes an emotional response on multiple levels.

Objectives: Catch the attention of viewers or those passing by and let them know that accidents happen that are out of your control. Therefore, having insurance can be beneficial and help make a stressful situation a little more bearable.

Target Market: Anyone that owns property (car, home, business, etc.) that could/should be insured.

Desired Actions: Visit and learn more about everything they have to offer including insurance for those times that “life comes at you fast.”

Value Proposition: The value proposition is that Nationwide will be there for you during extreme circumstances such as the one depicted in the ad. Many things in this life happen that we cannot control. Having insurance will make those stressful situations less stressful.


(Formula Toothpaste)

Description: There is a gentleman on a white billboard who is actively pulling the advertisement off of the metal framing with his teeth. In the bottom left corner is a tune of Formula toothpaste and below it reads “builds strong teeth.” This ad also uses humor to catch the attention of the viewer.

Objectives: Show the viewers that Formula toothpaste makes your teeth strong and healthy. It is a refreshing and atypical toothpaste message as most toothpaste ads highlight the pretty smile with pearl white teeth.

Target Market: This ad takes a different approach and caters more to those who don’t care as much about the whiteness of their teeth but more so about the health and strength of their teeth. This is more likely to be directed towards the male consumer, but really it is aimed at anyone who brushes their teeth (which is hopefully everyone).

Desired Actions: Buy Formula toothpaste.

Value Proposition: Formula toothpaste will make your teeth healthy and strong. Strong enough to rip through metal as the ad illustrates.



Description: This is an ad for a rest stop restaurant in Austria. It surrounds the entrance to a tunnel on the highway so that viewers quite literally drive through the ad. It is a woman’s face with her mouth open like she is about to eat something. The open mouth serves as the tunnel entrance and the ad reads “all you can eat rest stop.”

Objectives: Let drivers know that Oldtimer has everything they need while on their journey to their destination. It uses humor, a massive face, and a strategically placed ad to make it impossible for drivers to miss unless they were driving with their eyes closed.

Target Market: Anyone driving on the highway who may need to stop for a snack or meal.

Desired Actions: Stop at Oldtimer and satisfy your hunger while on your trip.

Value Proposition: Oldtimer is an all you can eat rest stop made to help you satisfy your hunger while on the road.

Below you will find an analysis of 5 Magazine print ads that caught my attention. 


Title: Weight Watchers

Description: An extra-large frame door titled “Entrance” next to an extra-slim framed door titled “Exit” with the Weight Watchers logo on the wall in between the doors. This ad targets the emotions of those looking to lose weight by promising results.

Objectives: The objective of the ad is to show viewers that Weight Watchers is confident in their abilities to provide weight-loss results to their clients. The simple thought provoking picture gives viewers hope for turning their life around.

Target Market: Anyone looking to lose weight and become healthier.

Desired Actions: Look up or inquire more about what Weight Watchers has to offer to those looking to lose weight.

Value Proposition: The illustration shows the confidence Weight Waters has in helping its clients achieve results.



Title: Orion Telescopes

Description: The ad shows three snapshots through the lens of an Orion telescope. The first is of the moon. The second is a clear, zoomed in view of an American flag on the moon. The third is an even more zoomed in and still clear view of the stars and stripes of the American flag on the moon. Orion is an American company who prides themselves on having quality products for an affordable price. The use of the American flag certainly gets the patriotic emotions flowing.

Objectives: The objective is to show the viewer how powerful and clear their telescopes are.

Target Market: Anyone interested in astronomy or using telescopes or similar type products. They offer other products such as binoculars for activities such as birdwatching.

Desired Actions: Buy Orion products, specifically a telescope.

Value Proposition: Orion provides high quality optics with all of its products.


Title: Liking Isn’t Helping: Be a Volunteer

Description: This is an ad by Crisis Relief Singapore. This specific ad shows a child with an amputated leg lying in a bed. Surrounding the bed is a group of people and all you can see of them is their hand giving a thumbs up to represent a “like” on Facebook. In the bottom right of the photo you see the Crisis Relief Singapore logo, their website and a statement that reads “Be a volunteer. Change a life.”

Objectives: It is part of a campaign to illustrate that simply liking a page or post on social media is not actually helping. It is encouraging viewers to volunteer to help a cause and not simply “like” a photo for their own peace of mind.

Target Market: I think the ad targets two groups of people. I think it will remind those who already volunteer to continue to do so as their help makes a difference. I think it also targets people who have never volunteered by making them feel somewhat guilty for always just “liking” posts.

Desired Actions: Visit the website and sign up to be a volunteer.

Value Proposition: By volunteering, you can help change the lives of those in less fortunate situations and make a difference in the world.


Title: Omax: Wide Angled Lenses

Description: A man is taking a photo of some birds by a pong. Just off to his side are two young, pretty women laying on a blanket. In the bottom right corner, you have the Omax logo and the words “Wide Angle Lenses.”

Objectives: This ad is part of a series of photos using humor and gender stereotyping to promote the benefits of a wide angled lens. It insinuates that the wide lenses cover angles so great that people around you wouldn’t suspect that they would be in your frame.

Target Market: Anyone interested in photography.

Desired Actions: Enhance your photography and buy wide angle lenses for your camera.

Value Proposition: The value proposition is that Omax’s wide lenses will capture more of your environment than traditional lenses.


Title: WE

Description: The simple light-beige background color is aesthetically pleasing and allows the black lettering to pop. In the center of the ad you see the word ME in caps and large font. The large letters definitely grab the viewer’s attention. The M is boxed in with dotted lines and a small set of scissors indicating to cut along the line. Below the large letters is a short list of how to build a lasting relationship. The list is a set of instructions saying to cut along the dotted lines and rotate the letter M 180 degrees. At the bottom of the ad is a statement that reads “If you want a stronger marriage, work on it together.” The website is also listed.

Objectives: Show the viewers that a successful marriage requires both partners to be working with one another to make a strong bond. It offers assistance to anyone who feels that they need assistance with their marriage.

Target Market: Anyone struggling with a marriage who is looking to make it stronger and needs some guidance.

Desired Actions: Stop being selfish. Work with your partner to create a stronger relationship. If you need guidance, visit

Value Proposition: cares about helping people build stronger relationships with their partners and has various methods for doing so.