Humans of Social Media

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Books have a way of transporting you to places and experiences through an author’s words. Reading an author’s review copy of wise guy by Guy Kawasaki reminded me of the wildly popular photo-essay series ‘Humans of New York’. Thought the books is organized like others – chapters and paragraphs – reading it doesn’t feel like the book filled with chapters and paragraphs, a story or plot. Instead, it feels like  Guy sitting down across the table from me, a glass of his favorite beverage in his hand and a dram of Whisky in mine.  And chatting!

The book took me through a journey through Guy’s childhood, teenage obsessions at college, the ‘tours of duty’ at Apple and his flirtatious yet committed interactions with the startup communities. Guy shares some of his aphorisms and opinions frequently on social media where millions read, some interact, some follow or retweet and many converse. He isn’t afraid of taking sides or sharing his opinion and seems to have adopted the ‘with great power comes great responsibility’ very well.  He admits his career limiting mistakes and wealth reducing missteps that still turned out to his advantage. I suppose when you are doing right by others, your karm do come back to reward you.
Though the book is peppered with hundreds of pieces of guidance, I highlighted a few and do intend to return to them often. I’m nearly certain to revisit

Don’t let people get to you, whether they are insulting you or not
Learn to like yourself, or change yourself until you can like yourself
The day after you start a job, nobody cares about your connections, history, and credentials—or lack thereof. You either deliver results, or you don’t
Changing your mind is a sign of intelligence
Learn to tell a story — Stories are better than adjectives because they are more comprehensible, memorable, and emotive
Do the right thing….. A formal contract with a dishonorable person is worth less than an informal contract with an honorable one

Imagine a book filled with stories about why the above sentences made a difference in creating Guy Kawasaki.
Needless to stay, like Guy’s other books like “Art of the Start” or “APE”, this book is a great first-read cover to cover and then a well-bookmarked reference. I have resisted loaning my “Guy” books because I am more afraid of losing my bookmarks than the physical book.
 

The Venture Educationalist

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Why do capitalists create scholarships?
I sat at my alma mater’s annual Scholarship dinner the other night. Hundreds of diners consisting of professors, students, parents, and donors enjoyed performances, listened to speeches, and conversed around their tables. Statements from the keynote triggered a thought and I drafted this post by typing in the title and the lede right at the dinner table.
Pi515 is a non-profit based in Des Moines, Iowa and run passionately by Nancy Mwirotsi. It seeks to deliver computer science education to children whose families sought refuge in our community. A remarkable lift for a vulnerable population in pursuit of life, liberty and happiness through education. The startup community in Des Moines recently connected to this non-profit through the leadership of Brad Dwyer and Ben Milne – technologists, investors, and community leaders who found reason to support Pi515’s mission and put their money and networks behind it. WHY?
Next Level Ventures, is a Des Moines-based venture capital firm that invests solely in Iowa-based companies. Its managing partner, Craig Ibsen is seeking to build a non-profit that would democratize computer-science education across the state while our academic infrastructure moves at its velocity to create the discipline. A state like Iowa increasingly depends on a shrinking workforce as it seeks to retain its role in feeding the nation through ideas and food and cannot wait for the academic deliberation cycle to find and deploy solutions.
Brad Feld, managing partner of globally respected Foundry Group and its many ventures, routinely invests in education through his personal and professional networks, including a personal match he and his wife Amy provided to Pi515 during a conferecne in Des Moines. His leadership in NCWIT (National Center for Women in Technology), Defy Ventures (inmate education), and more are representative of support for education at diverse intersections.
Fred Wilson of and Union Square Ventures routinely speaks about, invests in companies focused on, and invests directly in education focused on the sciences.
Back to Central College, the keynote speaker and outgoing chair of our Board of Trustees, Lanny Little, spoke of being able to attend college, create a remarkable banking and finance career spanning decades, endow his own scholarships for future generations of students. He was able to attend purely due to a scholarship funded by the family behind Rolscreen Corporation (now Pella Corporation of Pella windows). Why did a family focused on growing a global business in a tiny midwestern town choose to invest in a kid from Phoenix, AZ?
Lanny spoke about venture capitalists who invest in a different type of growth outcomes. Their outcomes aren’t as focused on a capital return directly to themselves; rather they focus on the outcomes to society through enabling education and viable careers for those who couldn’t otherwise afford a chance toward upward mobility. This mobility is clearly visible in the city of Pella where family philanthropy from Pella Corporation, Vermeer Manufacturing and other corporate partners has allowed several generations to educate those who often remain within the community thus ensuring its economic stability.
Similar investments are visible in the angel investor communities. Though created for capitalistic intent, many angel investments seek to grow businesses through a form of ‘for-profit philanthropy”, one referred to in this Brad Feld’s post circa 2006.
I am glad there remain altruistic and capitalistic reasons for investment in education, especially for those who are increasingly distant from it due to cost and social friction. I am grateful to the person(s) who chose to endow a scholarship that enabled me to attend college. And I am honored to know this breed of Venture Educationalists – capitalistic investors like Brad Dwyer, Ben Milne, Craig Ibsen, Brad Feld and others enabling K-12, college, vocational and non-traditional education.

As the community evolves, challenges persist

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I wrote this guest post for Clay & Milk after a wildly successful community conversation (Monetery) hosted by Dwolla. The original article is linked here and save in my blog for archival.
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Thank you Ben Milne for rebooting the conversation about our startup community during Monetery on March 20, your Dwolla team shined as a cohesive cohort of individuals.
I fondly remember from your launch events during the nascent days of Iowa’s startup community.
These are my reflections as an ‘aging’ member of Iowa’s startup community:
Brad Feld spoke for the first time in Iowa as a guest of Thinc Iowa conference in 2012. On the heels of Big Omaha and produced by its parent company—Silicon Prairie News—Thinc brought speakers from near and far. The event engaged about 400 people as attendees and sponsors observed one of the first startup conferences in Des Moines.
As a partner in now-defunct Startup City Des Moines, I sat and listened intently to messages from startup founders and advocates. Brad spoke from the heart about the newly introduced topic of Startup Communities, his eponymous book, and a nifty video produced by Kauffman Foundation. He followed up the conference talk with a fireside chat at Startup City with a couple dozen individuals from the community.
Fast forward to Monetery when Brad returned as one of the panelists to a Des Moines stage. As I sat in the back of the room once again listening to the same engaging Brad—whose blog I follow regularly—I couldn’t help but say to myself:

Things change yet they remain the same.

Des Moines’ startup community has grown significantly over the past six years. We have received an undeserved (in my opinion) amount of accolades and recognition, attention reminiscent of a future we want rather than a future we’ve developed.
Yet have risen, from the rubble of defunct incubators (StartupCity) or startups of 2012 (Pikuzone, Sharewhere, Real Estate Fan Pages, Mens Style Lab) such amazing entities as Global Insurance Accelerator, Funnelwise, Gravitate, Gain Compliance, Clinicnote and more. Geoff Wood remains the tireless advocate for the city’s startups and lone rangers; Mike Colwell has even more startups seeking his sage advice.
We have made amazing strides in connecting members of our corporate communities through these accelerators and brought several hundred (yes, several hundred) mentors who regularly volunteer their time and talent to grow startups. These have funded, bought the startups’ products and adopted the agile and nimble mindsets that are consistent with the startup lifestyle. Our chambers of commerce are no stranger to startup conversations and its leadership remains present, engaged and connected to new and established companies.
Des Moines may be a rare community whose chamber’s CEO is also an advocate for startups, invested in his own family’s startup (Homeditty) and knows the difference between startup (correct) and start-up (incorrect).
What hasn’t changed is the newcomer’s hunger for information. No matter the number of books, blogs, videos, guides and tweets, the new entrants to the startup community are seeking that early meetup, the startup weekend and the reassurance that there is funding for those who are sweating and bleeding on their way to success. There remains the same ‘failure rate’ from which new startups MUST be born.
The government is neither an ally nor an enemy – simply a feeder and supporter amongst many.
What we need is a continued conversation about these topics. Topics that will return to the Des Moines stage on April 5 with AccelerateDSM and then again in September with the Midwest Angel Syndicate’s meeting of angel and early-stage investors. Conversations that happen at Gravitate’s Full-Time Founders meetup. Conversations that need to happen at more venues, without relying upon Ben’s generosity (despite knowing that if he’s in town, he’ll likely show up and contribute!)
I’ve taken away the following from this recent conversation:

  1. When Drive Capital talks about funding 10 companies out of 3,500 applicants – they are exposing a very meaningful statistic – they funded 0.29 percent of the applicants. Startups need to do a LOT more to make their case for someone’s investment.
  2. Diversity remains a catalyst toward success. We, like a majority of the country, have a long ways to go to add this catalyst in startups, venture firms, cities, communities and teams.
  3. Awesome ideas, like Pi515, can starve to a quiet death without friends and allies. Kudos to Ben Milne and Brad Dwyer—who created a fundraiser last year for Pi515—for stepping up to the plate and writing a check that injected life into Nancy’s dream.
  4. We clamored for and got corporate partnerships. Now, the startups must step up, identify, and help solve the problems our corporate partners want solved.
  5. Let’s quit asking for reduced government regulation. If California can birth and incubate startups in one of the country’s most regressive entrepreneurial regulatory environments, regulation is a red herring.

Thanks, Ben, and the Dwolla team for the reawakening.

The probability of a Mea Culpa

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Approximately 28 years ago the department chair and a junior in his department entered into a debate. The style of debate wasn’t uncommon for a liberal arts campus and the professor seemed to cherish the opportunity to discuss a topic dear to his heart. The professor had taught multiple classes to me, the student, since freshman year at Central College.  That common area of the Math/CompSci department had hosted many such conversations and faculty were well aware of my preference for applied computer science. My disdain for the abstract and theory were well-known. The debate lasted a couple of hours and ended in stalemate.
Fast forward to this week when I spent a few days at an artificial intelligence conference hosted by O’Reilly. The conference was hosted by a book publisher focused on applied programming – from languages to systems, from the esoteric to the mainstream. A few hundred people came together to learn the concepts and applications in artificial intelligence to produce AI systems capable of machine learning.
It was a keynote by Peter Norvig , a director of research at Google, that reminded me of the three decade old debate. In the keynote, Peter spoke about the changing paradigm of programming from where we teach machines to “DO” to where we teach machines to “LEARN”. The learning achieved through probabilities assigned to outcomes. The binary trees of outcomes with a statistical probability. The literal mashup of Comp/Sci theory and statistics.  I realized then why I’d struggled with the workshops and some of the sessions. I was fine understanding the SQL queries and python code but was lost when it came to understanding the probabilities assigned to query results and analyses!
So, Dr. Meyer, you win. Our debate was about whether a Computer Science degree was earned without classes in statistics. You maintained that it wasn’t as Statistics was a core member of the curricula. I disagreed and seemed to remain right for 26 years in the profession. If I am to proceed any further into the reaches of AI and machine learning, however, I must first begin with a mea culpa and then put my liberal arts education to work and reopen the book on statistics before delving further into AI and ML.

Archive | Segregation isn’t the solution to lack of diversity

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I submitted this rebuttal to an article in Clay & Milk on May 16, 2017  and am saving it here on my blog for archival.

Sometimes you set aside your vulnerability just to curtail chances of preventing harm. As a guy who frequently sees the stories about a lack of women at the table in venture capital, I too wonder why. As a state comprising of a fairly even male to female ratio of workers, it is puzzling to see why more women aren’t investing as VCs and angels, especially since many Fintech employees in Des Moines’ are women.
The recent Clay & Milk article, “Making the case for female-focused investment firms in the Midwest”, highlights the core problems as there being simply too few women partners at venture funds and too few venture funded companies have women CEOs.
More investment groups focused on women-led businesses and women-specific groups for investors and strong communities were two of the solutions highlighted. I’m not sure that would work to solve the original issues.

A brief history

I was exposed to many of our city (and state’s) startups during my time at StartupCity Des Moines.  The core problem of access to capital led several of us to the table to discuss options, one of which was simply a directory of capital resources. The directory’s limited success led us back to the table and formation of a Des Moines based Plains Angels investment network. At its onset its membership saw as many as 125 members, 14 of which were women.

Progress

The network grew and, over its 4 year history has made 19 investments from 400 applications. As I reviewed applications, I looked for the business growth characteristics, capabilities of its leadership team, and the financials. Not once did the demographics – men, women, foreign-born, native-born, black, white, Asian or any other diversity factor come into play because they weren’t relevant to the investment.  As I look back, four were led by women – a datum I know only because I went back to look.
I believe our city is different from the larger cities of the coasts and elsewhere in the world. Either due to size or relative economic homogeneity, we have been lucky to operate more as a melting pot than larger cities like Chicago, New York, and London (England). We’ve largely avoided the separation inherent in a little-India, Chinatown, little Italy or mini Mexico here. Our city’s diversity is distributed throughout Des Moines and suburbs.
As evidenced by our own citizens and others, we are a prosperous and growing community.

Our strength, therefore, is not in division but unity.

One of the basic tenets of sound investment philosophy is diversification. Any investment in a vacuum is an island in itself.  Removal of bias is necessary to make sound investment decisions. The removal of bias happens naturally during investment discussions amongst a diverse group at the table. Investing, as a discipline, is agnostic to gender, geography, culture, religion and age.
Since the recent creation of women-only investment groups, I have seen Plains Angels membership of women fall. The group that once had up to 14 women in the room, 3 extremely regular, now rarely sees one. And without diversity of opinion over time, I can see the group dwindle further; a receding tide lowering all boats.
I strongly urge my fellow female angel investors, government sponsors and non-government organizations to collaborate not separate. We have wonderful examples of cities around the world that have struggled with these battles when it was too late – cities such as New York, Sydney and London built up cultural enclaves as the ethnic groups populating them supported from within, propped up new entrants, and removed the early struggles of language, economics and religion. Clustering, which once was part defense and part survival, now displays indelible borders.
As alluded to by the original article, women engage in deeper understanding of an investment. It also states that despite deep professional expertise, women aren’t yet used to making such angel investment decisions. Assuming both to be true, wouldn’t it be beneficial to engage in dialogue across genders, geographies and experiences? Better investment decisions can be made when men and women come together to harmonize their diverse ways of thinking, acting, researching, and evaluating. The silos being constructed in our community aren’t the way to achieve harmony.
If an end goal is more women partners at venture funds, let’s not begin by separating men from women.
Segregation doesn’t work as a mechanism to resolve lack of diversity. It makes it worse.

Liar-in-Chief

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I found myself at an unlikely venue the other night – a high-school basketball game. Though never a sports spectator, I was there to watch the high school dance team perform. Watching the game was, well, my ‘pre-game show’.  The first game had strong teams, fairly matched, and the visitors maintained a leading spread by 3-5 points. Sometime around the half-time point, the tables turned. Our team began to lead. Not by much but 2-3 points. Consistently.
It didn’t take much to see why – the opposing team was committing more fouls and our team was using the resulting free throws effectively. This continued to the fourth period and, with a few minutes left in the game, an edict came from the visitors’ coach – ‘no more fouls’. Fouls ceased, game returned to normal, and after two overtimes, the visitors won.
The integrity of the game, once restored, allowed the stronger players to perform, and their team to win.
I was watching a political volley of such fouls today from Kellyanne Conway on “This week with George Stephanopoulos”. She remained consistently belligerent in trying to defend and cover up statements of suspect truth. Seasoned journalists and panelists on a subsequent debate remained baffled by the strategy. Like Ms. Conway, they wanted the conversation and debate to rise above reality TV yet were encumbered by the responsibility to report on the facts and call out the lies when obvious.
It was the following sentence that made me connect the current politics to the basketball game –

Now we’re in a position where every time Sean Spicer takes the podium or the president says something, they don’t need to just be fact-checked, you have to presume that they’re not telling the truth.
-Stephanie Cutter, panelist with Stephanopoulos, 1/22/2017

Think about this for a second – when the pattern of bending or ignoring the truth becomes the new normal, then the only final conclusion is that NOTHING stated by the President or his official spokesperson is trustworthy. Just like every offensive or defensive strategy of the basketball game is supposed to be suspect for a foul first, strategy second.
I hope the President’s office can shake the contemporary moniker of “liar in chief”, lest the White House be reduced to a sorry farce.

The culture of romancing the automobile

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It has been an interesting week of car conversations. The topic emerged as I needed to replace my own car when its predecessor started being my teen’s mode of transport. Coincidentally, the topic has also remained front and center due to a variety of car related conversations. How can a tool evoke such myriad emotions?
My personal relationship with an automobile is purely practical – a safe and reliable way to get from point A to point B. A bluetooth adapter and accessible controls always win above the horsepower or look/feel. A faux wood trim seems as pointless as the skeuomorphic designs of bookshelves on computer tablets. The time and money on rims and trim, underbody lights etc have never appealed to me but I marvel at those who keep a love for it and support an economy here and abroad to support that hobby.
Converstion 1 – with my own family as I was looking to replace my four-year old Camry. I researched and test drove a few cars, including the Mini cooper. The small MC seemed to depart from my usual car, efficient in its recent rendition, safe per those to test that stuff, and fits four. I see it on the road in cutesy renditions and thought why not give it a shot. The test drive took me back to the cars of 70s and 80s – the closest memory that of the Ambassador cars in India. Loud, uncomfortable, rough and downright blah. 2 miles of test drive and it was back at the dealer. We would go back to the brand that had been comfortable and get the smaller vehicle to fit what I needed.
I heard of similar practicality from another friend who buys vehicles for his farm and doesn’t mind a $80K Range Rover through muddy stream and gravel lots – a truck built for that environment and not for the pristine suburbia where its brethren are washed weekly to display the badges of honor. A truck that is at serious odds with the Ford, Dodge and Chevy variations on the adjoining farms.
Conversation 2 – with friends who are techies and love the computers that now drive the cars. I was surprised to be a part of a conversation that spoke of a desire to buy the one badass, loud, rumbling engine one LAST time before the battery operated automatons take over and not a Tesla! Nerds, cool nerds, eschewing tech for the rumble. This is a group that wouldn’t just buy a Tesla to show off its prettiness and eco-cred, but want to hack it with modifications. One who’d buy every gadget to monitor aspects of the car and share it on custom built websites and report the car’s behavior to bespoke home automation systems.
Conversation 3 – with friends whose cars and trucks are additional tokens of prestige. Where a Lexus, Mercedes or BMW SUV is purchased to show that you are at par with your neighbors. The position in suburbia where a desire for conformity drives the home purchase, the career choice, the car, and even travel. A conformity born as part of the American dream. Conversation where the questioner wondered why I would buy a 30K Prius if I could easily afford a loan on a 80K asset?
The disconnect was clear — a car is a position in society – a Lexus no different than my Camry. I was buying for the green cred not to show off the amount of green I could spend. I was still buying my car to be at a place in society.
Cars in my world are not assets. They are a tool to move me (and fellow passengers) from one place to another. Unless I start using my car on the Uber network to transport passengers for money – the car never generates income for me (the definition of an asset – one that creates money). At best, my car protects my ability to earn. It depreciates the moment I drive off the lot and continues to do so for its entire life.
As Americans, our infatuation with the automobile is a century old. This infatuation has traversed the oceans and is now shared in places where guts (England – power!), glory (China – prestige), and practicality (Europe – smaller cars for smaller streets and commutes) drive purchases. I wonder, though, what the current generation of teens will do with this infatuation – will they perpetuate it in their own way or, like other skins of their predecessors, car ownership will fall the way of home ownership, nuclear family, suburbia, and corporate employment.
I will continue to ponder as I watch a friend rebuild a 60s Porsche from frame-up, watch a fellow electronics geek drive a low-riding powerhouse, and watch previous car owners ride a bicycle on a 20-mile commute each way in Iowa (until the weather wins).

Barley and coffee-magical spirits of people and place

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I just finished watching Caffeinated, the story of people behind the mighty coffee bean. Originating in a thin tropical band at just the right altitude around the globe, the end-product of the bean ends up as espresso, americano, drip, pour-over, lattes, and more. As I sat listening to the stories of farmers in Nicaragua, Ethiopia, India and beyond, told through translators and purveyors of fine coffees in US, Italy and elsewhere, I couldn’t resist drawing parallels to my other favorite spirit – Whisky.
Coffee grows as a berry, and looks suspiciously like a cranberry on those plants. The bright red shell protects the sugars and bean contained within, clustered in various stages of ripeness. When separated by color, size, shape, and smell, the beans are extracted, allowed to ferment for 27-32 hours, washed, dried on concrete surfaces, and packed away for shipment. Arriving at culinary centers around the world, the coffee bean (white, in color) is roasted for a perfect aroma, sheen, and readiness for grind. What ends up in our cup is a marvelous drink – sweet on its own, intoxicating in its own way, and communal in spirit. Additions like milk and flavors address the palate in fruity, woody, and body.
Barley seeds are immersed in water to allow them to open and release their sugars. Dried on concrete floors for 48 to 72 hours, some are infused with smoke from peat for their own aroma. Yeast converts the sugar to alcohol, ready for a drink. Allowed to relax patiently in wood, the spirit adopts the flavors of the casks. Enjoyed in communal celebrations, the spirit is enjoyed globally. So much like coffee.
The thing that struck me in the movie was how the farmers are resistant to change. A coffee plant may reach production ability in about four years – an eternity of risk before rewards are available. The story no different in whisky producing regions that religiously protect everything from the malting process and the shape (including dents) of the still to maintain uniformity. Unlike coffee, whisky has an even longer patience test – often lasting seven or more years.
If you subscribe to Amazon Prime, movies about both drinks are available as Caffeinated and Whisky.
Ancient processes to produce drinks that mark the beginning and end to a perfect day.

Entrepreneurship lessons and takeaways from the movie, Joy

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We saw the movie, Joy, last night. I’ve enjoyed the onscreen chemistry between Bradley Cooper and Jennifer Lawrence in previous movies, and this particular movie, based (loosely) on a true story offers another opportunity to enjoy these fine actors. Though (this is not a movie review) the first 30ish minutes are excruciatingly slow, once the story of entrepreneurship and inventing takes off, you will be hooked.

Industry rags have already created their listicles of “5 lessons” from Joy, and “lessons entrepreneurs can learn” from Joy. In my role as mentor and investor in startups, I notice items in current startups that Joy experienced as told through the movie. Here they are in no particular priority order.

  1. Pick your advisers carefully – we naturally turn to our parents, relatives, friends, siblings and business associates for advice. However, advice from a family practice attorney isn’t appropriate for patents, and a bookkeeper doesn’t necessarily make the COO. A parent’s natural role is to protect you from perceived and real adversaries – not exactly the person who is prepared to help through risk-assessment.  Joy’s best advisers ended up being a close friend and ex-husband – who do you trust?
  2. Read your contracts fully – you needn’t be an attorney to understand the minutiae of legal docs. Your legal counsel exists to understand the documents fully. But you as the business owner need to read each of your documents cover to cover. Yes, that includes the operating agreement (30+ pages), the patent application (100+), the tax rules (pub 515 is at least 76 pages), and any contract with a vendor, employee, partner, co-founder, and even the real estate lease for your office. When shit hits the fan – you’ll  need to revert back to these very documents. Having read them during peace, they’ll be far easier to manage at times of duress.  Though Joy managed to get through the minutiae during severe duress in the movie, this is not a common occurrence.
  3. Receive input from many, but decide from within – be the basic building block of our bodies – the cell. Receive input from all directions – positive and negative. Collect the various inputs without defending or supporting. Then, when you’re ready, find your place of solace, close your eyes, filter the inputs, and make your decision. Joy makes such decisions while shooting at a range, alone in her bedroom, scared witless at a hotel, and confident on a street. The place of solace will change, but your nucleus is constant – focus and decide.
  4. No one cares about your business EXCEPT you  – Employees, shareholders, investors, advisers, friends are all there in good times and bad, but their focus is forever on themselves – their job, their investment, their dividends, their billing and reputation, and their social standing. So, while you may be focused on growth, survival, collapse, payroll, contract, customer and security – they are not. So, survival depends on your ability to perform perfect CPR. Growth depends on your ability to spot opportunity. Collapse depends on your strength to perform euthanasia. Employee payroll may take money away from your own paycheck. Your business -> you are responsible.
  5. The littlest pieces of your entrepreneurial journey are worth cherishing – this one got me at the end of the movie. Through the early years of your journey, the tiniest elements set your direction. They may be a sketch, a photo, a piece of clothing, whatever. They were important then and will be imminently important in other parts of your journey.  Keep a time capsule through the journey and visit it occasionally. You may be surprised at the feelings that capsule unleashes.

In the end, it was a movie. Probably 50% true story of Joy Mangano and 50% artistic license derived by David O’Russell.  It was entertainment but left me with enough parallels to daily life that I felt worth sharing. Worth a matinee investment.

The critical elements of a term sheet

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The “Term sheet” carries an air of mystery and intrigue in the entrepreneurial community. Founders are either nervous or giddy about them, want to get one and celebrate its arrival. Investors are eager to sign them (while tending to wait for a lead investor to generate them).
Working with startups and angels in my community gives me a perspective on term sheets.  Since the landscape that governs capital here is markedly different than that in VC hotspots, I’m sharing the elements I see ignored/problematic/contentious, here, in Des Moines, Iowa.
Disclaimer: Getting introduced to Brad Feld’s Venture Deals, following a number of blogs, and ultimately digging through dozens (hundreds now?) of term sheets, I feel like the 4-10 page document is boiled down to a few critical elements that trip up entrepreneurs and angel investors alike. I am not a VC, nor do I represent a fund, so the motivators behind VC decisions are still largely remote to me.
Oh, and also – I am not a securities attorney – use this as a starting point in your journey on term sheet education but seek competent advice at the time you begin working with these documents.
What is a term sheet?

When an entrepreneur chooses to accelerate the journey of building or scaling a business with outside capital, the term sheet is a formal document that outlines the summary terms of exchanging a portion of the company (equity) for cash from an investor (investment). Though filled with legalese about a variety of important topics, it sets the initial terms of engagement, specifically through core elements that would fit on a napkin.
Untitled
The elements boil down to three simple drivers –  economic, team and control. Drivers that control the money aspects of the transaction, those detailing the people building the company, and how the power will be shared once the investment is initiated, respectively.
Economics (equity, valuation…)
Though it should come later, this is frequently the starting point of a negotiation.  A placeholder for the amount the two parties think a company is worth, valuation is a key point of the negotiation. Of course, like any parent, the entrepreneur values their company higher than the dispassionate observer. Similarly, the investor tries to justify the entrepreneur’s assessment or comes up with their own yardstick for evaluation. The mid-western investor rarely puts down a $1M or higher value on a company that has no product, no real customers, and an incomplete team. Ideas alone seem to rarely receive outside funding, and when they do, the term sheets are skewed toward a great deal of control in the investor’s hands for significant share of equity.
What’s an entrepreneur to do?  If the desire is to raise local money and not travel nationwide pitching to investors, then appealing to the local investors motivators is key. Those motivators, at this point in time, are product, revenue, and team:

  • Product – a company needs a minimum viable product (MVP) that demonstrates the founding team’s vision. It must be usable, demonstrable, available on the relevant platform (web, mobile, physical goods etc.), and one or more customers be able to speak to its viability and use.
  • Customers – Revenue comes from customers, so this is important. The history of a product’s sale to an unrelated customer — one with whom the entrepreneur didn’t have an established relationship –is important. Customers provide external validation of an idea and are key to an investor’s ability to preview a product’s market viability.
  • Team – a complete team is generally a pre-requisite for a company raising funds and must include founder (with a concrete role – not just title) marketing, product development, and ability to execute. These people and roles will change over time, so, a complete team needs to reveal the people who fill to roles to adequately guide the minimum viable company to the market where their products are sold, licensed, and used by real customers.
  • Exit – there will be discussion, however premature it may seem, about the liquidity or liquidation event. It could be brief, or a full buy-sell analysis, but there will be one. READ THIS CAREFULLY, especially the section related to liquidation preference that establishes rights to the funds received at a liquidity/sale event.

Team
Though the term sheet will have a signor on behalf of the company, the team does not need titles like CEO, CTO, COO, etc. At this stage, there really isn’t a true CEO or CTO – but rather founders, builders, designers and hackers. The first developer on a team will very likely NOT be the CTO of the fully baked company — the skill sets for the two are vastly different. Similarly, the founder will very likely be replaced as the CEO over the venture-backed lifetime of the company. The team, therefore, needs to be able to present a diversity of opinion that will lead the company to grow, but show a unified front through consensus building.
Rented CEOs and other titles are a let down – angel investors invest in passionate founders, and founders who have given up critical equity for a part-time CEO in early stages of building a product can actually hurt themselves. So, for the purposes of showing off the MVP and raising capital, founders (not a bunch of rented suited professional CEOs) should demonstrate their wares .  Business attorneys do a far better job negotiating terms.
Control
Once money and equity exchange hands, those providing the money will often desire control over the operation of the company in material areas. These terms change the daily behavior of the company and its founders, and must be negotiated early and clearly. If legalese in the documents is not understood, clarify – it’s a lot easier to do before the deal is done than after.  Any attorney worth their salt understands that the legalese in the documents is a necessary evil, and can summarize the entire document in a page of plain English. That page is worth its weight in gold for us mere mortals.  Key elements of control include such things as

  • Information rights – this gives the investor a right to receive regular (quarterly or otherwise) updates from the company that summarizes financials without divulging too much information that may be proprietary. Though angel investors have significant insight into a company and operate like many insiders, this right is still necessary to document and usually a requirement for an angel investment.
  • Founders salaries – investors know that the first influx of cash can alter the incentives and behavior in a company, including such major items as founder compensation as well as minor items like benefits. Thus, term sheets may dictate how much or if the founder can give themselves a raise.
  • New stock/dilution – investors understand there will be dilution during successive raises but want to have a say in when/how much/rules surrounding such raises. Expect a clause allowing the angel investor to participate in future rounds to maintain their ownership percentage, participate in sale of stock by the founder, and advance warning about upcoming events that can cause dilution.
  • Board Seat  – though many investors would love to be on the board for their new portfolio company, angel investors in particular, frequently decide against it and choose to serve instead as informal advisers, rainmakers, network connectors, and  supporters. Still, a paragraph or two will be dedicated to this element.

In closing, remember, a term sheet is not the final definitive document that guarantees an investment. It is simply the first formal document used to begin the conversation. Treat it with care.
 
Additional Resources
Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist
Ideal First Round Terms, Chris Dixon on cdixon.org