“Tell me about Holly.”
“Oh geez. Launch right in, why don’t you?”
“I want to know more about you. Tell me how she came to work for you.”
“Not much to it. She’s the little sister of Cassie, my best friend from junior high and high school. Pretty much a little sister to me, and every bit the pain in my ass that implies.” Kade spoke with obvious affection, belying the last words.
“She mentioned she’s been your only assistant.”
“I didn’t want one. She essentially let it be known that as soon as she graduated from college, she’d be working for me.”
“Definitely sounds kid-sisterish.”
“I think she had a bit of misapplied hero worship back then. I started my first company in order to help her younger brother, Sam, do better in school. He had a terrible time until he was diagnosed with dyslexia. It was ridiculous for such a gifted kid to be left to struggle for so long. Why wasn’t this part of every child’s health assessment? Why should it be any different than a hearing or eyesight issue?”
Jen knew the basics from her post-Maui research. “So you developed a program that quickly and effectively diagnoses kids early on.”
Kade nodded. “Along with some talented software developers, yes. Of course it didn’t really help Sam.”
“But it’s helped a lot of others. Both your companies have, from what I understand.” Jen remembered reading that Kade’s second venture stemmed from a bad accident involving a man who’d been like a father to her. He’d recovered, and Jen didn’t recall his name, but now she’d bet anything that the man was Holly and Sam’s dad. The company had developed a hemostatic gel people could carry around as easily as hand sanitizer, which could stop severe bleeding in seconds. Jen had some in her purse.
“I like to think so.”
“Then I don’t understand why her hero worship was misapplied. Sounds spot-on to me.”
Kade frowned and set down her fork. “She should have blamed me for Cassie. I don’t know why she never did. None of the Kellers did.” Kade slowly twirled the stem of her flute, seemingly studying the bubbles dancing upward to pop at the surface, her thoughts clearly unpleasant ones.
Cassie had been near the top of the list of subjects Jen had wanted to cover this evening, but Kade’s reaction changed everything. She didn’t want to push Kade, who was obviously pained by her memories. She decided to switch topics, but Kade beat her to it.
“How did you meet Charles?” Kade asked, pushing some salad greens with her fork as if gauging her appetite.
“He was an investor in a friend’s company, and she introduced us. Having heard their horror stories of working with VCs, I’m somewhat anxious about taking VC money.”
This statement seemed to nudge Kade out of her doldrums. “I’m familiar with Charles’s opinion on the subject, but what happened with your friend?”
“Same thing that happens to most women who aim for both a tech career and a family. She was considered a liability almost as soon as she announced her pregnancy, to the extent that she was for all intents and purposes ousted before she hit maternity leave.”
“We have laws against that.”
Jen scoffed. “We have laws against child pornography and drug trafficking, too. Doesn’t prevent it from occurring.”
“If that truly happened to your friend simply because she was pregnant, she had a bona fide claim against the board.”
Did Kade truly believe her words, or did she expect that all women ought to be able to succeed the way she had, if they just worked hard enough? With all of Kade’s years in the Valley, Jen found it difficult to believe she could be so naive.
“The filing of which would have immediately sunk any prospects she might have had to head up another company. Her reputation would have been decimated. You know damn well we’re in a white-male-dominated industry. It’s hard enough to be taken seriously as a female entrepreneur. A female entrepreneur with children? Nearly impossible.” “Impossible” was the word that stilled Jen’s tongue, as the next ones that formed in her mind unkindly related to Kade’s workaholism, and she didn’t want to go there. Yes, she believed women like Kade to be setting an unachievable bar for other women to emulate, especially those with kids. But Kade wasn’t to blame. The real issue was that society as a whole regarded the bar a realistic metric in the first place. The scale needed to be revised and leveled out between men and women, and needed to include child and senior care in the equation.
The table fell silent, and Jen wondered if she’d gone too far. She’d never been shy, and standing up for what she believed was, for better or worse, one of the things that gave her the chops to be CEO. Kade took another bite of pasta and chewed it thoroughly. Jen hoped it meant she was giving the matter due consideration. She highly respected Kade’s opinions—her real ones, not those she mentioned off the cuff as if from some sound bite.
“I assume this conversation is off the record?” Kade asked.
Given Kade’s position at Matlock, it seemed a fair question. “Kade, nothing you and I discuss is for public consumption. I consider you a friend.” Another subject Jen wanted to broach.
“It’s something I’ve struggled with. I joined Matlock because of their track record and reputation, and because I’m at ground zero for getting new technologies launched and in the hands of people who need them. But it doesn’t come without its own, well, how do I put this delicately? Sexism. I’ve considered starting my own fund and centering it on women-owned and women-led businesses.”
All of Jen’s concern about Kade’s willingness to be as thoughtful and open in private as she was at work melted away. As Jen considered a Kadrienne Davenport-led fund that supported women, she felt an uptick in her affection for her that she let show.
“What?” Kade asked, repeatedly smoothing the napkin on her lap as if uncomfortable with Jen’s reaction.
Almost giddy now, Jen said, “Yes. One hundred percent, yes. Fantastic idea. Oh, Kade, you have to do it.”
“I hate to disappoint you, but it’s only an idea. Nothing’s in the works.”
“Nothing about that idea disappoints me, and I would very happily accept an investment from such a firm,” she said with a wink.
“Depending on the size of the investment, you’d report to me. Longer term. Still interested?”
“Spoilsport,” Jen said, making Kade laugh.
Dinner passed too quickly for Jen’s taste. Although they’d covered many subjects, Jen had shelved several important ones so the evening wouldn’t turn too serious: Cassie, Kade’s father, her obsession with schedules, the no-date rule. On the positive side, Jen had zero interest in adhering to Kade’s dating edict and didn’t think it fraught with emotionally charged territory, so she decided to start there. She could push the rest out to the coming weeks, a future in which Jen fully envisioned Kade taking part.
Jen surveyed the dessert menu, but the rich pasta was filling, and she wanted to enjoy the comfortable temperature outside. “Do you want dessert, or can we walk? We can grab a decaf next door and stroll downtown.”
“Let’s do it.”
After purchasing their coffees, Jen took Kade’s elbow as they walked. She was in a good mood, feeling lighthearted from their discussion and thoughts of Kade potentially advocating for entrepreneurs like her one day. She decided to act like a CEO and take charge. “Can we talk about the no-date policy?”
This conversation starter didn’t seem to work initially, as Kade carefully sipped from her cup, eyes forward. “What would be the point?”
“Is it a religious thing?” Jen asked, ignoring her.
Kade laughed. “Hardly.”
“You’re not attracted to me?”
“What do you think?”
“I think you are. So then tell me. Let’s go through your list.”
“There is no list.”
“One. I don’t make enough money.”
“I don’t care about that.”
“Didn’t think s
o. Two, you don’t like my career.”
“How hypocritical do you think I am?”
“Three. You have a fiduciary duty to the shareholders of Creative Care.”
“I do.”
“Resign. Charles knows a lot of people who could serve on the board.”
“It’s not very professional of me to tell him I need to resign because I want to date you.”
“It’s more professional to remain on the board when you’re dating the CEO?”
“We’re not dating.”
“A fact that should change. Four. You like being alone.”
“I’m good at it.”
“But you prefer it?”
“I prefer not to hurt people I care about.”
“So you care about me.” Half statement, half question.
“Not at the moment.”
Jen laughed. “We’ll come back to four.” As they passed a bench, Jen sat and tugged Kade down next to her. She held her coffee in one hand and took Kade’s hand with the other. “Five. You’re adorable.”
Kade frowned. “That’s not an objection.”
Jen laughed again and lightly bumped her shoulder against Kade’s. She set her coffee on the ground and took Kade’s hand in both of hers, folding it into her lap. “No. I got distracted.”
“You’re agitating.”
“You think I’m cute.”
Kade sighed. “Five?”
Jen wiped the grin off her face and eyed Kade seriously. “I’m not worth it.”
“Not funny.”
“It’s not meant to be. I want to date you, we’re attracted to each other, and someone else can take your board seat. So you must think I’m not worth it.”
Kade tried to pull away, but Jen held her tight. “Help me understand.”
Kade drew an audible breath. “It’s the opposite.”
“What do you mean?”
“I’m the one who’s not worth it. Trust me. Please.”
Jen didn’t understand. Few people Jen knew were as competent and capable as Kade. How could she hold herself in such low regard? What had happened to give her such a poor opinion of herself? The desperation in Kade’s voice to close the subject left no room to doubt Kade’s sincerity and prevented Jen from pursuing the matter.
Kade untangled from Jen’s loosened grip and stood. She held out her hand.
Jen bent down for her coffee and took the hand that pulled her to her feet.
In a role reversal, Kade took Jen’s elbow as they started walking again.
Jen walked silently at Kade’s side, arm in arm. Confused. It was like some perverse version of the classic Just Friends breakup speech: It’s not you, it’s me.
“Do you know what the two best things about Maui were for me?” Kade asked.
“Your awesome new bikini and the hordes of admirers who hung on your every word?”
Kade laughed. “I did score an awesome bikini actually, but no, not even close. You, first and foremost. And, for a day, forgetting who I am.”
They walked on for several more blocks before Kade stopped in front of a shoe-store display. She pointed to a pair of sandals by extending her cup in its direction. “Cute.”
But Jen’s mind was racing. She could barely comprehend what Kade was talking about because she was back on Maui. Yes, Kade had said she wasn’t acting in typical fashion during their day together, but she was funny, warm, gracious, and kind—characteristics that don’t suddenly pop up for a day and then disappear. They might be sides to Kade that she didn’t express as often as she had that day, but they were hers, and they were genuine, as tonight again confirmed.
She wanted to ask Kade who exactly she was being now, because as with Maui, she liked this person. A lot. She liked that she was motivated by helping others, employed a family friend and instilled within that friend incredible loyalty, and willingly provided support and guidance to Jen on the business front. She warmed at the affection in Kade’s voice, the gift of her words just now.
Jen had no desire to play the long-suffering girlfriend to someone emotionally unavailable, damaged. She already played the role of caretaker to her grandmother—she didn’t need to replicate that in her love life. But Kade wasn’t emotionally unavailable. Jen remembered well many of Kade’s words.
You’ve been an absolute gift to me.
Few as special as you.
You, first and foremost.
She had to think through the best way of revisiting this conversation. Kade obviously had put up a wall, but Jen hoped she could find a window. Or a strong rope with a grappling iron.
Aside from an occasional comment one of them would make on something in a shop’s display, conversation died down, with Jen sensing that Kade, like her, was lost in her own thoughts.
During the ride back to Kade’s, Jen found she was conflicted about how to say good night. She wanted to kiss Kade, but she didn’t want to push her over the no-date rule to the point that Kade wouldn’t agree to another evening out. And if she were to kiss her, she didn’t want a fumbling exercise in the car. She wanted more.
She parked but didn’t shut off the engine. “Thanks for tonight, Kade. And thanks again for the meetings. I appreciate it.”
Kade reached toward the driver’s console and turned off the engine. Then she got out, walked to Jen’s side, and opened her door. “Can I have a hug?”
Jen delighted in the innocence of the question. It highlighted for her the sweet side of Kade she’d spent part of the evening remembering. She took the hand Kade extended and swung her legs out of the vehicle.
Kade pulled her into an embrace that they indulgently let linger. Finally, Kade pulled back into the circle of her arms. “Thanks for not pushing.”
Jen had been on the brink of doing just that. Holding Kade had felt damn good on Maui, but the Kade she’d known then was merely an outline—a quick sketch of an attractive woman who’d shown flashes of wit and kindness. Lately that framework was being filled in with greater detail, and the portrait emerging was that of a complex, beautiful woman whose intelligence and sense of humor were enticing Jen to want to see the whole picture. Now, having Kade in her arms felt so marvelous, it seemed cruel to have to let go. “Don’t think you’re getting off so easily next time.”
“Next time?” Kade asked with a crooked smile.
“You don’t think I’ve gotten where I am by listening, do you?”
Kade laughed. “Is that the secret?”
Jen reluctantly released Kade and folded into her seat.
“Good night,” Kade said, before closing the door.
Chapter Nine
Kade had made a lot of mistakes in her life. To this, she could readily admit. Sometimes she wondered if her two startup-company successes had come down to either sheer stubbornness or dumb luck. The number of things she’d done wrong as CEO was one reason she’d decided to move into the VC world, so she could mentor others. Many books, including her own, offered guidance: problems to watch out for, how to hold effective meetings, metrics to follow, recruiting advice, etc. Yet Kade believed the best defense against committing major errors was to listen to the specific issues her companies faced in real time and provide the kind of customized advice that generic articles and blogs simply couldn’t replicate.
But one of the biggest mistakes she’d made was having dinner with Jennifer Spencer again, because she couldn’t extricate her from her thoughts. By acquiescing to one-on-one time together after work, Kade was muddling messages. Asking Jen for a hug hadn’t helped clarify things either. It was unprofessional. Board members did not embrace.
Jen had a way of drawing her in. Jen didn’t have to flirt or ask or demand. She just had to be herself, and Kade was rapt. With one glance from those brilliant sky-blue eyes or flash of her captivating smile, Kade’s shields dissolved. She hadn’t abandoned all her precepts, but it had taken massive willpower to limit their good-bye to the hug she shouldn’t have asked for, when she ached to kiss Jen again. While she was in Jen�
��s arms, inhaled her scent, absorbed the warmth of her body, she felt enveloped by Jen’s tenderness, and she was lost.
They hadn’t communicated since their Tuesday dinner, and this was a big week for Creative Care. The product team was set to deliver version 1.0 of the mobile app today, designed to simplify matching seniors with caregivers. With the platform live, the skeleton referral system she and Jen were putting together with her hospital contacts, and the manual matches the company had been making over the past couple of months to seed the system with its initial transactions, Creative Care would put itself in much better shape to secure funding.
Although hitting the deadline to get the platform live had been Jen’s primary objective of the past few weeks, Kade was surprised when Holly told her Jen had requested that she not schedule any hospital-administration meetings this week. Creative Care needed to be moving simultaneously in multiple directions. Surely landing another referral partner was worth a few hours of Jen’s time? Jen wasn’t one of the staff writing software code.
But why was Kade keyed up? Each of the companies she invested in via Matlock Ventures was undoubtedly feeling the pressure of an important deadline. Startups always had a big customer to try to land, a new software feature to release, an important recruit to close, a marketing campaign to launch, an investor report due. Week in and week out, startup companies could be counted on to demonstrably act on material initiatives that, in the bowels of larger entities, would languish for months. It was one of the most-cited reasons employees gave for joining a startup—they felt they could contribute directly and quickly.
The difference, the reason why her concern over the state of things at Creative Care was a problem: it wasn’t one of Matlock’s investments. She was paid—and paid handsomely—to invest in, monitor, and advise the companies in her Matlock portfolio. She was a partner in the firm, for God’s sake. Yet here she was, colossal idiot that she was, wondering how Jen was faring, wondering how a team in which she didn’t have a dime invested was progressing.
Twice today, Holly had had to prompt her to jump on scheduled conference calls. That simply never happened. Both times she’d joined three minutes late, which to Kade might as well have been an hour. Her distractedness was causing her to violate principles she held dear. Arriving late to meetings was disrespectful and wasteful, two things she loathed. And today she’d disrespected colleagues and wasted their time because she couldn’t get Jen out of her thoughts.
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