Category: 1. The Deal is Dead

This is Act I. Maura and Syfon had seemed to be cruising towards the holy grail of startup goals, getting funded. They’d done the summaries, done the pitches, launched, and got some evidence of traction and validation. But nothing is ever that simple. Suddenly, the deal is dead.

Please Call

January 2020

Until the “please call,” Matt Kenny was having one of those special Oregon mornings he dearly loved. Up early, close to dawn. Quiet house. Janet sound asleep for another hour or so, to be wakened up when one or another of their daughters would probably call. His Mini-Cooper, iPod playing slow sixties folk rock, radar detector on, quietly urging him to enjoy the empty streets (hence the radar detector) with a sharp turn, a quick burst of gas. The landscape in shades of gray and dark green typical of cool and cloudy mornings in Eugene.  Layers of clouds settled into the forested hill like fingers. Ground fog clung to the flat meadow of Amazon Park two feet over the ground, five feet high, like some kind of ethereal blanket. In the distance, a small break in the clouds lightened Spencer’s Butte, speckled with off-angle sun. He stopped on the way, as always, at the coffee cart where they knew him and his daily order, and kept his signature on file, so he could skip the clipboard step. He kept quarters in the side of the door, one per day, as a tip. Life was good.

He loved his office in the early mornings, before the others arrived, before the phone calls. Just him, the keyboard, the computer, his coffee, and his “mellow morning” playlist loud, no need to plug in the damn earphones. Folk, folk rock, blues. Emmy Lou Harris singing Boulder to Birmingham. Sonny Terry and Brownie McGhee singing Bring it on Home to Me. Another new day. New emails. Blog posts. His metrics too, blog subscribers, Twitter followers, the brave new world of constant scorekeeping.

But this morning it didn’t last. His phone showed a text from Maura Benson:

“Please call as soon as you can. Deal’s dead.”

Damn. He’d heard a beep from his phone while driving, then forgot it as he parked and set up in the office

There was no ducking Maura. She was totally 2020. Maura, communicator par excellence, techie, social media maven, and thorough. Matt, however, had a whole lot of the 80s and 90s still in him. And he wasn’t always quick to answer.

Still, he didn’t call immediately. He first sat back, sipped his coffee, focused on the pine tree a few feet outside his second-floor window, and watched the cars starting to show up, just one at a time, on the corner of 11th and Ferry, below his office. He closed his eyes, took a long deliberate slow breath, and exhaled. He listened to another slow country rock song. He got ready to call about bad news.

He didn’t believe the deal was really done. He expected to convince her that she was over reacting. She’d already had two fabulous sessions with the angel investors. And, more important than just the sessions, she had a real business started. There was real need, a real market, great potential. Her team seemed strong. Matt thought hers was one of the strongest deals they’d seen in years. Great product-market fit, huge potential market, scalable, defensible, and a great team.

He’d learned the pause first from of decades of “please call” messages from Janet, his wife. They’d reach him in hotels during his too-frequent business trips when the kids were young. The calls back followed a pattern. Matt, exhausted by clients, tension, taxis, airports, and hotels, would call Janet, exhausted by kids, lunches, homework, bedtimes, messes, dishes, cooking, shopping, overwhelmed, waiting for him to call, anxious to share some disaster. He’d think he was thousands of miles away, also exhausted, having nothing but work stress. She’d think he was done with his day and alone in a hotel. He’d often say one wrong thing or another, going defensive. Then he’d feel like a five-year-old kid with lunch all over his ill-fitting shirt as Janet hung up angry. That would kill the good feelings he’d get during lonely travel by dreaming of Janet naked and happy. Those were not the best times between Janet and him. Work, stress, sleep deprivation, and distance do not make couples’ hearts grow fonder.

After he settled himself, Matt called Maura.

It Can’t Be That

Matt’s return call caught Maura driving, in traffic on the beltline, with Jack in the back seat. She’d wanted to talk to Matt all night, but she rejected the call quickly, almost automatically. Why? Her finger was faster than her head, leaving her with a lingering question, which she felt but didn’t voice, not even silently to herself, in her head. Why not? She needed to talk to him. He would help her track down the problem with the deal. Why not answer?

She would have loved to talk the night before, after Jack was asleep; but couldn’t talk in the middle of the morning rush, getting seven-year-old Jack to school.

All night she replayed that last meeting with the due diligence team. She was in shock. Before that, she and her startup were the darlings of the season, shoe-ins for the half million dollars the SWAG angel group was getting ready to invest. What happened? Sabotage? Bad faith? Could she prove her software was really hers? Didn’t she develop it as an employee at TK? And why was she hiding her legal problems?

Would Matt know anything? He might. He knew most of the SWAG investors. He was pretty much tapped in. But he’d never let on about any worries, had never seemed concerned. And she couldn’t call him yesterday early enough to really talk. She had to pick up Jack, then dinner, and bedtime for him, and then it was too late.

But when Matt’s call call rang in over the bluetooth in the car, she didn’t realize at first that she didn’t actually want to talk to Matt; at least, not yet. She was anxious to talk about the deal problem when it first came up. But in the meantime she’d grappled with what she feared was the real problem. One she didn’t want to mention.

First thought: Problems. Bad news. There’s traffic, I’m distracted, and I’ll take it later.  Too much going on. Am I afraid of bad news?

Second thought: Jack was in the back seat. Car calls were speaker calls. But he was plugged into his Kindle fire. She often took calls like that.

Realization – or was it worry: Donald. That recurring image of Donald promising revenge, the night she moved out. Standing, arms folded, filled with ice-cold resolve. Not sadness, not regret, not even anger. Empty but for desire to punish. And bone cold.

She’d spent all night stewing, avoiding voicing that worry even to herself in the middle of the night. This was angel investment, Syphon, a new startup, nothing to do with Donald. New life. And the investors loved it. Didn’t they?

Maura, going on four years now since the divorce, never ever talked about divorce or Donald to anybody but family and closest friends. She hated the thought that she’d look predictable, like the stereotypical divorced mom blaming things on her ex. That wasn’t her.

Besides, she’d told herself, repeatedly, nobody who didn’t know Donald well would believe her stories. Far fetched. A divorced woman blaming her ex. So predictable. Trite. She was better than that. She never shared stories. When asked, she was deadpan. Yes, divorced. Yes, a seven-year-old son. Single mom. Change the subject. She hated talking to outsiders about Donald.  And who would believe her anyhow?

She wanted to think she was just being paranoid, which is what she told herself, as Jack fiddled with the playlist on her phone, not talking, leaving her to her thoughts. Why take it back to Donald? It was business.

She tried not to, but kept going back to the memory of Donald, three years earlier.

“You will regret this for the rest of your life,” he told her. “I will make your life miserable.”

He stood at the top of a small flight of stairs, a few steps between different levels in his (it was never really theirs, always his) trophy house. She carried a box of essentials she’d need to stay with her parents. He watched carefully, silent, arms folded, like a parent watching a disobedient child, or homeowner watching a household servant suspected of pilfering silverware. He was tall, wore glasses, had wavy brown hair over a high forehead. By then she had long forgotten his original air of the stereotype nerd, the brilliant computer geek, the successful entrepreneur. He’d taken on a new cloak, his fictional version of the stern all-powerful, all-knowing, higher being.

She knew, without question, from her bones outward, that Donald’s promise was not an empty threat; it was simple hard truth. Donald wasn’t angry, at least not the way normal people are angry. This wasn’t going to go away like it would have with nine out of 10 fathers angered by the mother splitting up with them. This was Maura blowing up Donald’s carefully constructed fiction in which he was the Internet millionaire, she the beautiful blonde, the parents of Jack, the happy couple.

So she let the call go. Not now. Not in traffic. Not with Jack in the car, she thought. I’ll collect myself first, then talk.

Periférico

Damn. Stuck in traffic again. Celia hated the traffic in Mexico City. She sat stopped dead on the Periférico, which had been built as a high-rise freeway connecting the north and south of the city along its west side, but had been a glorified parking lot for years.

She tried to just breathe, inhale and exhale, and wait. But there was a special claustrophobia to traffic jams. Would she be stuck for hours between exits? It happened to her a few times a year. Just a couple of months earlier she left Carlos’s office at McKinsey in Las Lomas, just a few hundred meters from the Periférico entrance, at 3; and was stuck between exits on the Periférico for almost four hours. Celia believed in the soft voice of Gil Fronsdale from the Zencast podcasts, the calm, just breathing, peace. But damn! Not when stuck in traffic. Not with the fear of sitting there. And would she have to pee? Could she hold it? Try meditating that, she told herself.

She also told herself she should have just stayed in her apartment and dealt with Maura’s puzzling message. Why risk the traffic? She liked her office better than home mostly for bandwidth, and her main computer, plus the camaraderie.  She worked better there than in the cramped apartment down in Santa Teresa. But damn.

She did have decent cellphone bars, at least. She rechecked Maura’s message in Whatsapp:

“We need to Skype. The deal is in trouble.”

She did call in Skype, immediately, but Maura didn’t answer. She guessed (correctly) that she was taking her kid to school. She knew she was a single mom. So she decided to take off for the office in the meantime. Damn. Bad guess. Bad traffic.

Mexico City. Her home. Her birthplace. Where her mom, her sisters, and their kids lived. She loved them, loved the memories, but hated the city now. Maybe the world’s largest city, but who could count. The largest is either this one, Shanghai, or San Paulo. She’d been to San Paulo once, found it like Mexico, sprawling, ugly, smoggy, livable only for people like her mom and sisters, rooted there. Shanghai looked pretty in pictures – mainly at night, with all the lights. She’d seen scary pictures of Shanghai’s smog during the day.

Traffic remained still. Parking lot. You could literally get pizza delivered while stuck in traffic. They used motorcycles. She remembered the TV skit, people selling their car stuck in traffic to buy one that was stuck closer to their destination. Being caught again put a lump in her throat. Worry about Maura’s crisis. She couldn’t lose Maura, it was the best job she’d had in years, and they connected so well. And there was hope of getting back to the U.S. if Syphon took off.

What could Maura be worried about? She’d seemed very optimistic, almost euphoric,

She flashed back, often, to that time in the plane, just a year earlier, sitting with Carlos of course, both of them recently graduated from Stanford, her with the CS degree and Carlos the MBA. They were both from Mexico City, but they’d met at Stanford. They were married, basking in family, back home over the previous summer. But they’d lived on campus at Stanford. Which was paradise compared to Mexico City.

That memory wouldn’t clear. As the plane took off from San Francisco, they held hands.

“Oh no,” Celia said, softly. “Are we really going back?” She felt mostly dread. She wanted Carlos to cheer her up, remind her, his job was great, they’d be rich, they’d live close to the office, in Las Lomas, tree lined, nice apartment, close to work, immune by being walking distance from all the commuting. But Celia couldn’t help it. After four years at Stanford, it was like going from a bright well-lit place, sunshine on the mostly brown hills, bicycles on wide campus paths, to a dark dystopia, smog and traffic.

She’d forced herself to go along with it. For Carlos. For more than a year, since they became a couple, they’d dreamed together about his MBA recruiting season. It was the ultimate happiness, like Samuel Johnson had said, which was the anticipation of happiness. Profs and counselors reinforced the dream. Recruiters confirmed it. They were going to be rich. When that turned out to be McKinsey Management Consulting in Mexico City, Carlos was so proud. He’d landed a prime job, a status job, better than all but a handful of his MBA classmates. McKinsey was the best. It meant salary, company car, even school tuition when kids came. And mobility. Carlos talked of levering the Mexico City Celia loved Carlos so much it hurt and she wasn’t going to

Carlos smiled ruefully, squeezed her hand, loved her soft touch and brilliant eyes. Loved her also when she was quiet, pensive, like she was right then.

Maura, Driving, Alone with Sadness

With Jack dropped off, Maura headed back towards downtown to meet with Matt for coffee. Alone, driving, she let herself fall into sadness. She felt the lump in her throat.

She’d fought that temptation most of her life. Then a friend – it might have been Janet – passed on a second-hand suggestion, something she’d heard in a zen podcast or maybe read in a blog post:

“We’re programmed to fight the sadness,” she said. “That doesn’t work. You have to have the emotion, acknowledge it, let it live there in you, and swim in it. Then it flows through you, and you go on.

So Maura did. Her eyes moistened, but she still changed lanes and made her exit. She remembered her illusions, in college, her early dating, the romantic comedies and love stories, the dreams and fantasies. She’d never had the schoolgirl moments, not even in the beginning. Dating, fiancé, bride, honeymoon, she’d waited for passion that never came. She had passed forty without ever coming really alive, not even for a few minutes, with that kind of love. Would that never happen?

But she had Jack. There would have been no Jack without Donald. And then she had to find a parking space and go find Matt in Café Sienna.