Category Archives: Startup


Why Startup CEOs Still Have to Make Sales Calls

by Howard Tullman


It’s not your strength, or maybe not even what you enjoy doing. But being there to close the deal isn’t something you can simply hand off to the sales team.

At what point can a CEO turn sales over to professional salespeople?  Before that can happen, the company has to achieve two foundational milestones:

  • You need to know exactly what you’re selling—by doing it over and over again (and not as a one-off).
  • You need to know for certain that others can sell it consistently.

That only comes with the maturity of your product/service.  Until it reaches that point, stay in the field and keep selling.  Your product is still being developed on the fly and continually redesigned/reconfigured to better suit the real requirements and demands of customers.  The fact is, ultimately only you can make the critical design and development decisions and you’ll do a much better job of that if you are hearing it directly from the end users and not from a bunch of whiny salespeople.

I’m seeing more and more startup CEOs who discover way too soon that they don’t like the wear and tear, the travel, and the rejection that are all crucial parts of selling a new product or service.  So they retreat, thinking they can run their businesses while they’re sitting on their butts behind a desk back in the office. That’s not how this game works; that behavior is a formula for failure. You may not be an extrovert.  You may not even know the technology that underlies your business as well as half the other people in the company.  You are, however, the boss and today that fact alone means a lot, at least to the people who make the final purchasing decisions.

Remember—buyers are typically older than you, they grew up in strictly hierarchical systems where titles count, and they need to be made to feel important and respected if they’re gonna sign off on your deal. No offense to any of the members of your team, but customers don’t want to deal with the monkey—they need to see the organ grinder. That’s you. And they want you for all the obvious reasons:

  • People don’t really care how much you know until they know how much you care. Show up. It’s important.
  • Startup staffs are notoriously scattered and hurried—lacking focus and attention to detail. Customers want to know that you personally are connected, paying attention and directly engaged with their business, their concerns, and their problems.
  • Clients want to hear it from the horse’s mouth. Not second hand. They want commitments and assurances from you. Everybody knows that the sales guys will say anything and promise them the world.  They need assurance that you will stand behind your product or service and make good on your promises. The buck always stops with you.

Product Maturity

Once your product/service reaches those critical milestones, it’s time to kick yourself upstairs and focus on other things. I encourage CEOs who find they spend too much effort selling to optimize their time.  I suggest that they find competent sales managers and others who can tee up just the right meetings for them—not opening meetings which are a dime a dozen, but closing meetings where the deals get done.

Finding sales meat-eaters to fill managerial roles isn’t easy; they are the hardest hires for any startup, but it’s absolutely critical to have them onboard if you’re going to build a viable business.

When your startup is hiring talent, you need to avoid certain categories of salespeople. For example, stay away from what I call empire builders.  There’s a whole generation or two of sales management types whose experience comes only from large organizations.  I have found fairly consistently that they are the wrongest guys possible for a startup because they grew up in a system where they measured their value and their success by the sheer number of people they managed rather than the results that those folks delivered. Nothing kills a young business faster than bloat and bureaucracy and having too many sales people sitting on their hands and not selling is the worst kind of poison. So be careful what you wish for and who you hire for this critical job.

There’s no more challenging job than being the CEO. You are responsible for the health of each part of the organization and the trajectory of the entire venture.  Stay in the sales loop until your product/service matures.  Then focus on closing deals.  Customers need you to be there—to say what you’ll do, and do what you say.


 Howard Tullman is the CEO of Chicago-based 1871, where 500 digital startups are building their businesses every day. He is also the general managing partner of G2T3V and Chicago High Tech Investors, both early-stage venture funds; a member of Mayor Rahm Emanuel’s ChicagoNEXT Innovation Council and Governor Bruce Rauner’s Innovate Illinois Advisory Council. He is an adviser to many technology businesses and an adjunct professor at the Kellogg Graduate School of Management.


This article is an excerpt of one that appeared recently in Inc.

Image Credits – Getty Images, MS Office, Howard Tullman

Chicago Venture Magazine is a publication of Nathaniel Press Comments and re-posts in full or in part are welcomed and encouraged if accompanied by attribution and a web link. This is not investment advice. We do not guarantee accuracy. Please perform your own due diligence. It’s not our fault if you lose money..Copyright © 2018 John Jonelis – All Rights Reserved


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by John Jonelis

“Tell me a story, Uncle John!”

“A story eh?” My pal Loop Lonagan got in big trouble telling stories to Jim Kren’s little girl. “Y’know, Princess, in this case, maybe discretion’s the better part of valor.”

“But I always get a bedtime story. I can’t sleep without a bedtime story. Please, Uncle John! Pleeeeeeeeeze!”

How can a guy turn this kid down? “Okay Princess, just lay back and pretend you’re sleepy.”

“Make it a Christmas story!”

“Hmmm.” After a moment, one occurs to me—one I can steal. “Okay Princess, here goes. There’s this bright guy I know. Immigrant entrepreneur. I mean, Princess, he comes to this country and founds a startup company.”

“I know what it means.”

“It’s high tech. Agricultural analytics. Starts it during the dot-com crash around the turn of the century. Despite the lousy economy, it takes off big-time, goes public and makes me and the other investors real happy.

“His two sons work for him to build up the business. They’re his key employees and make fair salaries. The company adds a mobile app, enhanced AI, and thrives right through the 2008 recession. Years later, it’s still strong. Stock keeps going up-and-up.”

“That’s not a Christmas story, Uncle John! That’s business stuff. You sound just like my daddy.”

“Hold onto your red fur hat—I’m just getting warmed up. Papa loves those boys more than anything—wants them to run the company when he retires. Lost his wife years ago and these two are all he cares about.

“Now let’s look at the younger son. He knows he’s gonna inherit a lot of stock some day and can’t want to get his hands on it. He feels trapped and longs to run his own life while he’s still young. So on Christmas in 2006, he announces he wants his inheritance—right now. Like most kids that age, he’s full of himself—not seeing things from his fathers point of view, maybe not considering all the ramifications of what he says. But it’s kinda like telling the old man, ‘I wish you were already dead so I had your money.’”

“That’s not nice.”

“No it’s not and it gets worse. The young buck’s not interested in the company at all. Not planning to stick around. Just wants to cash out and enjoy life.”

“This is a bad boy, Uncle John.”

“Ah Princess, don’t be so hasty to judge. You don’t know what’s really in his heart. Now the company’s listed on Nasdaq, and Papa still owns 40% of the shares. He says to himself in his broken English, ‘That what they want? Okay!  Is Christmas!’ There’s a family trust set up, so he simply transfers his stock—all of it to the two boys.

“Right away, the young colt sells his stock on the open market. With all that loose cash, he feels rich. So he moves to Vegas. Lives the wild life. Gambling all night. Show girls. Maserati. Yacht. Private jet. Hangs around with movie stars. And lots of foolish investments that don’t pay off. He never calls or writes home. Doesn’t visit the next Christmas.

“Now the older brother is still working at the company. But as you might have guessed by now, the old man is really the brains of the outfit. The shareholders—especially that big VC firm that owns a lot of stock with a seat on the board—they all want to keep Papa running the company. The board of directors votes to keeps him on as CEO, with a fat salary—bigger than he ever paid himself.

“Now I want you to notice something: That move wrankles the older brother. He secretly wants to run the show, but there’s nothing he can do about it. So he hoards his shares and bides his time. He stays at his job, working harder and harder, trying to prove himself. Doesn’t like it that his father’s salary is coming out of his share of the company. Can’t wait for the old geezer to croak so he can slide into that big desk.”

“Ugh! How horrible! This brother is worse than the other one!”

“Right Princess. Pappy doesn’t have a clue what’s cranking through this guy’s mind. The kid works hard. He’s dependable. Therefore, he must be a fine boy, right? But he’s so secretive—so sour—never smiles—and for some reason that Pops doesn’t understand, the other one still holds a soft spot in his aging heart.

Back to the younger buck: By the second year, this kid’s portfolio takes a dive, and at the same time, he’s going through money like water. Kid starts looking for work. After all, he was a big executive at a successful company. Impressive LinkedIn resume and all. But now it’s the great recession of 2008 and all he can get are temporary consulting jobs. He forms a startup company, crunching numbers for big investment houses and actually raises some capital. But not enough. Goes belly up within the year. Figures he’s a failure and he’s ashamed to let his father know how bad things are turning out for him. So he doesn’t visit the family that Christmas either.

“By the third year, he’s broke, can’t pay the rent, and gets evicted from his hotel suite. Most of that year, he’s living in his car and scrounging food, feeling mighty low.

“Don’t cry, Princess.”

She sniffs. “This is a terrible Christmas story.”

“Wait and see. Finally, the kid hits rock bottom and comes to his senses. I mean—hey—he’s starving to death. He decides to go home. Even newbies at his dad’s company make a decent living. He’ll confess everything to his father—his failure, his waste—he’ll apologize and beg for a part-time job. Nothing special—maybe an internship or some low-level gig on probation—something like that. He knows it’s more than he deserves.

“Out of the blue, Papa sends him an invite to Christmas dinner and a plane ticket that year, so he texts that he’ll come. Spends the whole flight practicing his confession.

“On Christmas Eve, the old man gets restless; hires a limo and goes out to make a few preparations. Phones his secretary with special instructions. Stops at Mens Wearhouse and lotsa other places. Gets to O’Hare and hangs around for hours. I mean, this guy hasn’t even heard from his boy in three years! When the kid finally walks out the concourse, Papa runs to him, throws his arms around him, hugs him tenderly, tells him he’s glad he’s home. The kid hasn’t changed clothes in a year. Stinks to make your eyes sting. No luggage. Papa leads his son to the limo, arm over his shoulders, and tells his boy he loves him.

“In the back of the limo, the boy stammers out his practiced confession, tears streaming down his face, but his father will have none of it. ‘Stop—no more!’ he shouts. If there’s anything this kid ever learned, it’s to obey his father’s commands. Papa breaks out two tumblers and a bottle of Drambuie and leads the conversation into fond recollections and good times. Does most of the talking and the kid can’t help but laugh at some of the memories.

“Limo stops at the Union League Club and they take in a steam and swim and shower. The kid opens his locker to find a new shirt, jeans, sport jacket, shoes—the works. He can hardly believe it and again stammers out his confession.

Enough already! I not hear it!’ says his father, and the old man’s word is always final.

“When they get home, the place is full of Papa’s close friends and dear customers—maybe 300 people. A twelve foot tree sparkles with a million lights.  A live band pumps out Christmas music.  The aroma of good food fills the house. A caterer lays out an amazing number of enormous turkeys with stuffing and potatoes with gravy, and cranberry sauce, wine and all the trimmings. All that food takes up the big table in Papa’s baronial dining room and they set up a buffet line. People enjoy their meal milling around, indulging in lively conversation. When everybody eats their fill, out comes the pumpkin and mincemeat pies, ice cream, coffee, and brandy. The band leads the crowd singing carols. Take it from me: this is a great party! I for one, enjoyed every minute of it.

“Now the older brother works late at the office that night, as usual. One of the guests notices him out front, pacing in the snow. Papa runs out to him—doesn’t even stop to put on his coat. Begs the boy to come in and join the party. But the kid spits out words in anger: ‘I work for you day and night! I never refuse to do anything you say! Do you ever throw a party for me? But when this worthless bum—this son of yours—shows up, after squandering your money on women and gambling—you celebrate like some kind of idiot, disgracing us in front of all our friends and customers!’

“Papa hugs him and speaks softly to him in his native dialect. ‘On you I depend always. You are good boy. You own all my company stock. But your brother is home! After three years he come home! We must celebrate! Is like he come back from dead!’

“But the older brother won’t be consoled. He curses and shouts, ‘He should be dead,’ and gets in his car and drives off.”

I smile at Princess. She doesn’t look sleepy at all.

“What happens then?” she says.

I sigh. “The old man—Uncle Ludditis, in case you hadn’t guessed already—he eventually retires and opens that bar he always dreamed about.  Rents me the back room for my magazine.  The older brother takes over as CEO and forces the younger one out.

“Uncle John!  That can’t be the way it turns out!  It’s not fair!”

“Why not?  Those are the consequences of their decisions.  The older one holds onto his 20% share of the company so he finally runs that show, a rich miser living alone.  The younger one learns from his mistakes, finds employment elsewhere, marries a good woman, raises two wonderful children.

“And Princess, their father loves them both deeply, no matter what.  His love is all he has left to give and he’s not stingy with it.  Close your eyes now.  Merry Christmas.”

Story credit: Jesus Christ, The Parable of the Prodigal Son –Luke 15:11-32


More Christmas Stories:





Chicago Venture Magazine is a publication of Nathaniel Press Comments and re-posts in full or in part are welcomed and encouraged if accompanied by attribution and a web link. This is not investment advice. We do not guarantee accuracy. Please perform your own due diligence. It’s not our fault if you lose money.
.Copyright © 2017 John Jonelis – All Rights Reserved

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By: William Arrington

The original intent for this follow up to Hyperlocal Social Economies (HSEs) was to focus on how businesses can participate in these targeted consumption markets. I think this is an appropriate time to discuss how HSEs may evolve. Before diving in let’s quickly recap what comprises an HSE market:

  • A group of consumers with similar lifestyle and consumption patterns (i.e. friends)
  • Common set of goods/services consumed by the group
  • Competitive market for said goods and services
  • Goods and services are geographically unbound

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by John Jonelis

.In Chicago, we enjoy something few high-tech centers can boast—easy access to a primal wilderness—a vast paradise, ancient and unspoiled—unique in the world and very special.

Whenever I’m in this place, I love the world just as I find it.

A short commuter flight from O’Hare Field whisks me to Winnipeg International Airport. Then a short local flight delivers me to an isolated airstrip carved out of an untouched forest—hundreds of miles from roads and crowds. And I experience absolutely no jet lag. My destination is located within my own time zone! This amazing opportunity is accessible due to technology, and I intend to enjoy it as often as I can!

Canadian Shield shown in red

My favorite location is Manitoba at the 55th parallel—as far north as Alaska’s Aleutian Islands and the Bering Sea—as far north as Omsk. North of that grow stunted trees in permafrost, but here tall Pine and Aspen surround the lakes. Uncounted and untouched waters flow through this region—a massive system of rivers and lakes, draining into Hudson Bay. Here it is not uncommon for the ice to measure four feet thick as late as May. I come in June.

Boreal Forest—the crown of the Northern Hemisphere

Mark T Wayne kindly explained to me the geology of this place that I love so intensely. This is the unique and magnificent intersection of the Canadian Shield, and the Boreal Forest. The Shield is a vast area, surrounding Hudson Bay, where, during the last ice age, severe glaciation removed everything down to bedrock. The Boreal (also known as the Snow Forest) is a predominantly conifer range that rings the northern hemisphere like a crown. (In Russia, it runs through Siberia.) Canada’s intersection of Boreal and Shield makes up the largest unspoiled wild area in the world.

Overstressed Chicago entrepreneurs need a place to burn off the tension of a high-risk high-reward lifestyle. Some find solace at the golf course. Others in spectator sports, television, or booze. I prefer the stunning spectacle of God’s creation in the raw. And I bring my fishing rod!

The great Northern Pike reigns in these waters and grows to enormous proportions! Nobody stocks these lakes, but the waters teem with these ferocious predators. Conditions are just as they’ve been for thousands and thousands of years, and unlike other regions of the globe, Manitoba means to keep it that way. No live bait. Barbless hooks. All fish returned to the water unharmed. That transforms an idle pursuit into a challenging alternate activity for budding business tycoons.

Vladimir Up Yours Putin finds time to enjoy the Boreal in his native Russia—that is, when he’s not busy overrunning free countries or thumbing his nose at our great nation. If he can get away for such activities, I think Chicago entrepreneurs can do the same.

I’ve experienced many good fishing lakes in Canada’s provinces. This is my favorite. Knee Lake is a 50-mile-long body of icy water punctuated by rocky reefs and 150 islands. Only one small lodge operates here. They call it North Star Outpost and to me, it’s as close to heaven-on-earth as you can get.

Loop Lonagan, Mark T Wayne, and Donatis Ludditis from my magazine surprised me with tickets for this excursion. And I am immensely grateful.

Here, a man indulges in the elemental fight against nature and—for a precious time— entirely escapes the Chicago rat race!

Here, a man lives off the fat of the land, and—in a delightful exception to the catch-and-release rules—harvests fat walleye for that exquisite tradition known as Shore Lunch.

Nothing tastes better than fresh walleye cooked over pine logs. This is beer batter—my favorite.

In this ecosystem, nothing goes to waste. After that wonderful meal, I’m back hunting big pike.

Without warning, a strong strike sends a shiver up my elbow and shoulder. I feel vital life at the end of my line. The weight of it leaves no doubt that this is a trophy fish. Then a sharp pull almost yanks the rod and reel from my hands and the water boils!

I catch my breath and strain against the fish. This monster goes through all the escape behaviors learned over a life of perhaps 50 years. It jumps clear of the water. It runs deep. It rolls in my line. It thrashes, tugs, and splashes the surface of the water. Every time I catch sight of this fish, it strikes me with awe. This one is strong and thick. As they say up here, it has shoulders!

It charges the boat and I reel fast to keep my line taught. A moment of slack and the prize will be gone. It swims underneath me and I plunge my rod deep into the icy water and then work it around the bow. When I finally bring this fish to the side of the boat, it turns away and peels line off my big round reel at will.

This battle repeats three times. A fish this big does not succumb easily and expends all its energy before surrender to the net.

Quickly, I lift him into the boat. The barbless hook falls from its mouth. A hurried measurement—46 inches! One snap of the shutter and my prize is back in the water.

A fish this size is delicate and often will not survive the fight without help. Holding it by the tail, I move its body back and forth, flowing water through the gills. A minute or two, and the great northern pike strokes its tail free of my hand and swims away with power. I hope to catch that one again next year.

But for now, I must catch my own breath. This primal battle in God’s wilderness leaves me stunned and in awe and immensely satisfied.



This is North Star Executive Outpost on Knee Lake, Manitoba, a protected pike sanctuary.

Website –

Phone – Talk to Hope Levenhagen at 800-563-7151

Email –


Charts and Maps—Wikipedia.

Photography—John Jonelis.

Chicago Venture Magazine is a publication of Nathaniel Press Comments and re-posts in full or in part are welcomed and encouraged if accompanied by attribution and a web link. This is not investment advice. We do not guarantee accuracy. Please perform your own due diligence. It’s not our fault if you lose money.
.Copyright © 2017 John Jonelis – All Rights Reserved

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Filed under angel investor, Canada, Chicago Startup, Chicago Ventures, Entrepreneur, Entrepreneurship, fly fishing, Startup, startup company, vc, Venture, venture capital


by John Jonelis

Here’s a Chicago Area startup that brings pleasure, relaxation, and satisfaction to tired business people, gets them out in the open air, away from the pressures of the big city, and teaches them to smile again. Does that sound like a worthy goal?


I think so.

Now imagine you’re in waters bounded by trees of all kinds—not a house or building in site! No water skiers. No high-powered outboard motors. Not a boat of any kind!

Well, can you imagine that?


You see the flight of the blue heron, the bald eagle, ducks and geese. A couple of otters. Nobody in your boat sets eyes on another human being all day long! Sound good so far?


This is nature in the raw. You’re drifting a wild river—in strong current—strewn with huge boulders. As you make your way downstream, you shoot several rugged rapids. But due to the skill of your guide and his specialized boat, the ice in your martini glass is never disturbed. You feel at ease the entire day.


You bring along a hat, polarized sun glasses, a rain jacket, but no fishing gear. Your guide hands you an expensive Orvis 8-weight fly rod. It feels surprisingly natural and light in your hand.

Maybe you never cast a fly rod before, but your guide gives you a few pointers and moves the boat a little closer to the target—just to make it simpler for you. Now you’re casting hand-made six-inch streamers at the banks with ease. Soon you find out why the fly rod is favored on the river. It’s the most efficient tool for the job.

And fly-casting is therapeutic and highly relaxing.


Soon you thrill to strikes from trophy smallmouth bass that fight like a tigers. The fish here grow fat as footballs. Landing one in the heavy current on a fly rod takes all your skill and strength. I can think of nothing else that gives this kind of peace and satisfaction.





Yes, we all dream of exotic trips to faraway places. But this one requires no passport. No airplane tickets. All this is happening on the Wisconsin River—a three-hour car ride from Chicago!

Wanna go?



You gain entry to this paradise in an unusual little boat—a specially designed dory—incredibly maneuverable—easily able to withstand these rocky rapids.

Motorized aluminum rowboats and jon boats risk ripping open their bottoms and ruining their props and lower units on submerged rocks. Electric trolling motors are useless. These rapids swamp canoes and challenge kayaks. A $75,000 bass boat wouldn’t last an hour.

But the diminutive dory makes for safe passage and provides a comfortable and stable platform for you to cast your line with accuracy. It makes the raging water seem calm.


Your guide controls the boat with incredible precision using oars.


The specialized equipment and the guide’s skill allow you to gain entry to this paradise. Almost nobody else can get in here. That makes for very little fishing pressure. That means abundant game, eager to attack your offering. And the bass here are much larger than those found on famous rivers out east.

Now, THIS is what I’m talkin’ about!

Abe Downs—a chemist by profession—runs Great Northern Fly Fishing out of Stevens Point Wisconsin—just three hours north of Chicago. He’s an Orvis-certified guide and brings his scientific training and businesslike professionalism to bear alongside his extensive fishing knowledge. He’ll even get you a discount at a local restaurant.

Abe switches to musky with the fly rod in the Spring and Fall and scores a good percentage of the time. I love fishing musky but they’re called “The Fish of a Thousand Casts” with good reason. In contrast, these huge smalleys seem always voracious for a meal—even after a cold front! They fight harder than pike. And they bite in the summertime!

Okay, I hear the objections. This ain’t no startup because—because what? Because Abe doesn’t plan to grow like Uber?

Bosh! This little company may not present an investment opportunity for your venture capital fund, but it’s a startup all the same—and quite a successful one. He’s booked most every day of the season. Like a tech startup, he makes use of specialized technology and proprietary knowledge to operate the business. Few can compete in his niche.

And he brings pleasure, relaxation, and satisfaction to himself and his clients. Does that sound like a worthy goal?

I think so.


On one trip this summer, my fishing partner was my son. On another, it was my friend, Rod Erickson. Neither fished with fly rod and streamer ever before. Both learned quickly and—truth be told—out-fished me. I think Abe is a good teacher.

Photography by John Jonelis, Robert Jonelis, and Rod Erickson


Great Northern Fly Fishing


1020 Tree Lane, Plover, WI 54467


Chicago Venture Magazine is a publication of Nathaniel Press Comments and re-posts in full or in part are welcomed and encouraged if accompanied by attribution and a web link. This is not investment advice. We do not guarantee accuracy. Please perform your own due diligence. It’s not our fault if you lose money.
.Copyright © 2017 John Jonelis – All Rights Reserved

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by Howard Tullman

There’s no polite or easy way to say this, but winter is on its way in the venture world. It’s getting tougher and tougher for startups caught in the lukewarm limbo between ideas and invoices to get their early backers to up their bets especially when it’s not clear that they’ve found a viable business model and/or a way to stop the bleeding sooner rather than later. Too many pivots with too little to show for the dollars down the drain and pretty soon no one wants to hear your, “someday soon,” story or your next grand plan.


And if you’re not breaking even, no bank will look twice at your business or your balance sheet. This change isn’t restricted to the unicorpses in the Valley; it’s going on in every village where waves of wishful thinkers are starting to wonder what hit them.

My sense is that the smart investor conversations taking place today aren’t very often about the company going big for the gold or about the current investors doubling down so some startup can shoot for the stars. These increasingly cranky chats are less about excitement and enthusiasm and much more about ennui and possible exits. Because the two things that some early investors and every VC understands are sunk costs and opportunity costs.

While the entrepreneur is sweating survival, the investors are trying to decide whether their incremental dollars would be better spent on a new deal elsewhere. These are the days when easy money gets hard.

Those great gluten free sugar cookies (from the hip new bakery down the block that just shut its doors) are tasting more like ashes in their mouths and they’re asking themselves how they ended up sitting in a room with no doors feeling like some sucker after the circus left town.

The unhappy folks who are still sitting at the table (more likely associates now than the partners who got the ball rolling) aren’t talking about how much more money they can put to work; they’re trying to figure out how little additional cash they can put up to preserve what’s left of their position.


Everyone is telling you that they’re really not inclined to do much of anything at all if you can’t drag some new money from outside players to the table to help set the price and get the next round started. Flat valuations in times like this are the new “up” rounds and there are down rounds galore.

This is a Plan B world at best and the down and dirty talk on the limo ride to LaGuardia almost always includes whether to also shoot the CEO while they’re in the process of trying to clean things up and save a little face. So if you’re the one on the bubble, forget Plan B, and get started on what I call Plan C. You need to get a head start on talking about the tough choices and critical changes that need to be made.

It’s about figuring out what immediate actions you can take that will make a difference before they turn the lights out. You can have results or excuses, not both. Focus on facts rather than futures if you want to be there when things turn around.

And forget about playing the blame game – no one cares.

Plan C is all about choices: contraction, consolidation, combination, conversion, and concessions. The last C is closing the doors and that’s not a sight that anyone wants to see. So find out which of the C’s makes the most sense for your startup.



Just suck it up and admit it. You can’t be all things to all people and no one ever has been. Focus on what sets you apart and what represents the best prospect of a long term sustainable competitive advantage for your business and forget everything else. Don’t apologize, don’t try to explain, just buckle down and get the job done. The recent launch of UberEats in Chicago (as an “instant” meal delivery service) and its almost immediate abandonment of that commitment is a good example of knowing when to hold ’em and when to fold ’em. It doesn’t take a genius to figure out that it’s pretty stupid to open the umpteenth home meal delivery service in Grub Hub’s hometown.

Businesses that scale too soon and which are a mile wide and an inch deep are doomed for many reasons, but the clearest and most telling is that they can’t cost-effectively engage with, support, or connect to their customers because the customers are simply too few and too far between. It’s critical to nail it before you scale it and, if you’re grossly overextended, your business is going nowhere.



Shut down the stupid San Francisco office sooner rather than later. You had no business being there in the first place and the fact that you doing no business there ought to speak for itself. San Francisco may be the most overheated and least representative market in America. Everyone there drinks the KoolAid for about 10 minutes and then moves on. Building a new business there is as slippery and unstable as trying to nail Jell-O to a tree.

New York should be next on the list. NYC isn’t a city – it’s 5 or 6 different marketplaces all mashed together – with a million people just waiting to eat your lunch. Your business expansion needs to be driven by actual demand, feasibility and real opportunities – not by some investor’s fantasies and/or fables about life in the Big Apple foisted on the public by the media and by people barely making it in Brooklyn.



Take a careful look around and see who else in your space (or adjacent to it) is doing things right and see what the prospects of some kind of combination may be especially if your market itself continues to be more cluttered and competitive. We hear constantly that the shared/surplus economy or the “Now” economy continues to grow fueled by millions of millennials holding multiple jobs. But tracking the gig economy isn’t quite that easy. While the number of multiple job holders has in fact grown dramatically, the percentage of the number of people so employed as compared to the total number employed has been flat or down over the last decade.

We had a great example of a timely and smart combination recently in Chicago where Shiftgig and BookedOut got together and decided that there were all kinds of economies and opportunities in a merger as well as the sheer relief in knowing that they could stop trying to beat each other’s brains out in the market. They are both players in the increasingly crowded space which the Commerce Department is trying to define as “digital matching firms.

Shiftgig was bigger and better established, but BookedOut had a lot of momentum and was gaining important traction in the experiential marketing sector. Now instead of spending time building duplicative back ends and other redundant systems and offerings, they can bring a single story to the market in a cleaner, more efficient and less costly way. This is exactly the kind of story that all of their investors wanted to hear.

It’s not easy in any market to attract the technical talent, the motivated sales people, and the operations folks that you need to grow quickly and a well-planned and thoughtfully executed combination can demonstrably accelerate the process. You need to be careful to make sure that the companies’ visions are aligned and that the problems they’re addressing are similar and that the cultures of the businesses (and the leaders in particular) aren’t in conflict.

These things aren’t made or broken in the board room when the papers are signed, they rise or fail in the implementation and the execution. But in today’s world, it’s often a lot better and smarter han trying to go it alone.



Sell some of your stuff to someone else. You may be great at lead generation and lousy at closing the sale once those prospects show up at your door. Or you may be a great sales organization that sucks at fulfillment and customer service. When you look at your skill sets and your customers, users, clients, etc. through a different lens—looking at them as potential assets to be converted or sold to some other enterprise, it helps you see more clearly exactly what kind of business you’re building. It may make the most sense to look at your company as a conduit or an intermediary and not as a one-stop shop trying to meet all the needs of the marketplace. You’ve got to play to your strengths and build on those if you’re planning to stick around.



Maybe your pricing made sense in some early fever dream where you were the best and only player in the space, but now there are fast followers and clones everywhere you look and their offerings (at least on the surface) look a lot like yours. Once your customers start talking about price, you’re on a very slippery slope.



Here’s the bottom line. In the long run, you can’t save your way to success and it’s no fun to fire your friends or postpone your pet projects. But if you don’t survive during the difficult times, you and your business won’t be around to savor any success down the road. Do what needs to get done and do it now.


Big Gulp from Howard Tullman

About the Author

Howard Tullman is the father of 1871 and Matter—the huge Chicago incubators.

This article appeared previously in News From Heartland




BookedOut .


Chicago Venture Magazine is a publication of Nathaniel Press Comments and re-posts in full or in part are welcomed and encouraged if accompanied by attribution and a web link. This is not investment advice. We do not guarantee accuracy. Please perform your own due diligence. It’s not our fault if you lose money.
.Copyright © 2017 John Jonelis – All Rights Reserved

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Filed under 1871, angel, angel capital, angel investor, big money, Chicago Startup, Chicago Ventures, Economics, Entrepreneur, Entrepreneurship, Heartland Angels, Innovation, Invention, investor, Startup, startup company, vc, Venture, venture capital


by Mark T Wayne

We’re here to interview some reprobate named William Shakes for the job of special correspondent. I do not know why I’m a part of this. No sir! Perhaps it’s the strange nature of the recruit. Perhaps it’s because Jonelis recommended this particular…person, and does not entirely trust the judgement of Jim Kren, his assistant editor. (Shakes bears an uncanny resemblance and must be related in some way—maybe) Perhaps it’s because that execrable Lonagan creature is the only other help Kren could muster. But we need more writers, so here I am, eager and helpful as always, ready to lend any assistance within my power.

Mark T Wayne

Kren consults a wrinkled scrap of paper. I believe he’s reading questions from a list. “So, uh…your name is William Shakes. Is that right? Tell me about yourself.”

What kind of softball question is Kren pitching? There sits Shakes in frilly regalia, looking like something out of an Elizabethan play. He probably came here straight from an all-night costume party, roaring drunk, and Kren asks a fool question like that. Wait, I believe the man is transparent enough to respond to such utter inanity.

  • “What’s in a name?” he says with dignity. “That which we call a rose by any other name would smell as sweet. We are such stuff as dreams are made on. But if it be a sin to covet honour, I am the most offending soul alive.” Spoken fluently and with aplomb! And in a well-modulated voice!
  • Loop Lonagan looks at the man slack jawed. After a moment I hear him whispering to Kren. “What didee say?” Kren fiddles with his paper and mutters to Lonagan, “Idiot! I was gonna ask you that!”
  • My value to the proceedings is now clear. Not to mention that I recognize the true and somewhat illustrious identity of this candidate. “Gentlemen, Mr. Shakes expresses the sentiment that his name and his fame do not matter; that he brings to the table a strong imagination and boundless creativity. He’s proud of his accomplishments and liable to brawl with anyone that displays the audacity to criticize his work. (Also, gentlemen, notice that the man carries a sword.)”

“Why,” Kren asks testily, “didn’t he just come out and say what he meant?”

I express the opinion that’s precisely what he did.

Lonagan shrugs and grins at his boss. “Ain’t got no problem with it.”

William Shakes

Kren reads the next question:

  • “What is your greatest accomplishment?”
  • Shakes sits there in that hot scratchy outfit, seeming at ease. “Some are born great, some achieve greatness, and some have greatness thrust upon them,” He says. “The play’s the thing. Thirty Seven there be, wherein I catch the conscience of the king and posterity.” The man runs off these lines without breaking sweat.
  • More muttering and both Kren and Lonagan turn to me. I clear my throat. “He’s considered the supreme writer in the English language and highly respected throughout the known world. Among other things, he produced 37 highly prized major works of written material that have captured the attention of world leaders.” (Privately, I take violent exception to the widely-held belief regarding his supremacy as a writer.  Such accolade is more aptly applied to myself. But I refuse to squabble.  Honour is at stake. Yes sir! I will do nothing to lampoon this interview!)

A brief dumbfounded silence. Then the barely vocalized sounds of approval indicate that these two examples of lower life are suitably impressed by the response. I warm to the task! Kren scans his page of questions.

  • “What major problem have you had to deal with recently?”
  • Shakes: “A fool thinks himself to be wise, but a wise man knows himself to be a fool. It is not in the stars to hold our destiny but in ourselves. We know what we are, but know not what we may be.”
  • I immediately translate: “He says he’s learning not to underrate himself. As a result, he never shirks a task, even if he feels inadequate. Because of that, he’s consistently surprised by hidden talents.”

Lonagan finally gets up the nerve to ask a question himself:

  • “Are you one o’ deeze team players?”
  • Shakes: “Prithee, it be thus. Love all, trust a few, do wrong to none.”
  • Me: “Ditto that.”

Loop’s dog Clamps. No known photograph of Lonagan exists, but they look a lot alike.

Lonagan again:

  • “What’s yer biggest weakness?”
  • Shakes: “If you prick us do we not bleed? If you tickle us do we not laugh? If you poison us do we not die? And if you wrong us shall we not revenge?”
  • They both sit there stunned, so I venture another paraphrase: “He says he’s only human, subject to the same vices of body and character as you two.”

Kren throws up his hands, then with an obvious effort, composes himself, and manages to appear grave and somewhat skeptical. Then he plods on.

  • “How do you think you can add value to our magazine?”
  • Shakes: “There is a tide in the affairs of men, which taken at the flood, leads on to fortune. Omitted, all the voyage is bound in shallows and in miseries. On such a full sea are we now afloat. And we must take the current when it serves, or lose our venture.”
  • Lonagan: “What didee say dat time?”
  • I happily translate: “He says the magazine could go on the rocks due to poor staff and lousy management. But we’re at a critical stage right now and must take full advantage of it while the opportunity is ripe.”

That last answer emits a bit of grumbling between the two louts. Those fellows have no idea who they’re dealing with. Lonagan asks what I can only assume expresses the issue that bears most tenderly on his feeble mind:

  • “How much money d’ya want fer dis gig?”
  • Shakes: “While I am a beggar, I will rail and say there is no sin but to be rich; and being rich, my virtue then shall be to say there is no vice but beggary. If money go before, all ways do lie open, but the comfort is, you shall fear no more tavern-bills.”
  • I immediately insinuate myself: “He says he doesn’t come cheap, but he never pads the expense account.”

Kren utters a deep sigh and hits him with what I am sure is his final payoff question:

  • “Why should I hire you?”
  • “Our doubts are traitors and make us lose the good we oft might win by fearing to attempt.”
  • I try not to bust out laughing. “He says, don’t be a ninny.”

Kren and Lonagan stare at each other. Face it—they botched the interview. There is nothing remaining to discuss. No sir! Jonelis wanted this relic on staff. These goons found no reason to reject the man.

Kren shrugs. “Show up tomorrow for work. Eight o’clock sharp.”

Shakes gives a bow and a flourish. “Good night, good night! Parting is such sweet sorrow, that I shall say good night till it be morrow.”

As William Shakes nobly marches out, I can barely contain my mirth.  But tomorrow, the man will stand on the sidewalk for hours.  Our office rents space in the back room of a fine establishment and Ludditis doesn’t open the bar till the potato pancake connoisseurs crowd in for lunch.  Kren’s revenge.


Read the first in this series – TO BE OR NOT TO BE HACKED.

Image Credits – John Jonelis, Public Domain

Chicago Venture Magazine is a publication of Nathaniel Press Comments and re-posts in full or in part are welcomed and encouraged if accompanied by attribution and a web link. This is not investment advice. We do not guarantee accuracy. Please perform your own due diligence. It’s not our fault if you lose money.
.Copyright © 2017 John Jonelis – All Rights Reserved

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Filed under angel, angel capital, angel investor, Big Corporations, Characters, Chicago Startup, Chicago Venture Magazine, Chicago Ventures, Entrepreneur, Entrepreneurship, Jim Kren, loop lonagan, Mark T Wayne, Startup, startup company