Two IPOs, $444 million raised, historic week for Wayfair, HubSpot, Greater …

Eight days of exhausting, cross-country travel. Four newly-made multi-millionaires. Two local companies. It was a momentous week for Greater Boston’s tech startup world.

For a region determined to show the heavyweights in Silicon Valley and New York that this is a technology force to be reckoned with, having the executives of Wayfair and HubSpot ring the New York Stock Exchange bell one week apart, signaling that their companies were now publicly traded, was no small achievement.

The two companies raised a combined $444 million in their final, frenzied pushes, earning their cofounders and top executives fortunes and affirming their decisions to stay where they had started.

It was a dizzying journey right up to the final hours.

On Wednesday, Oct. 1, Niraj Shah and Steve Conine, the cofounders of Wayfair, the Boston-born online furniture retailer, woke up in Chicago for one last pitch to investors. Before they had left home a few weeks earlier for their national roadshow to raise money, Conine had to buy his first two suits.

Now appropriately dressed, Shah and Conine and their top executives flew to New York Wednesday afternoon. The two men gathered their employees and close family members for dinner at Harry’s Cafe and Steak, a short walk from Wall Street.

Thursday morning began a special routine that every company goes through before its initial public offering, or IPO.

It starts with cars arriving at the hotel in the morning and bringing the founders, executives, some investors, and other key team members to Wall Street for breakfast, along with a history lesson on the stock exchange.

For Conine, the emotions of that short trip from the hotel were unexpected. His father grew up working around the corner from the stock exchange, and used to take him onto the floor after hours. When Conine’s car rounded the corner on Nassau Street in downtown Manhattan and he saw the Wayfair banner draped across the front of the stock exchange building, he was overcome with a wave of emotions he said he wasn’t prepared for.

After the breakfast, the stock exchange president finishes by presenting the company co-founders with gifts and other team members with a special token to mark the occasion.

The Wayfair group was then whisked to the trading floor to prepare to ring the ceremonial opening bell at precisely 9 a.m. The company could barely fit the team it had brought down from Boston in the box above the stock exchange, but they squeezed in, and as Conine did the ceremonial deed, Shah clapped and beamed beside him.

One week later was HubSpot’s turn.

Like Wayfair’s Conine, Hubspot cofounder Dharmesh Shah, who only owned jeans, had to buy dress pants before embarking on their trip. The HubSpot executives all packed for a two-week stint, like a baseball team on a roadtrip, with the stock exchange as the final destination.

On Oct. 8, the day before their bell ringing, Shah and his cofounder Brian Halligan also woke up in the midwest, in St. Louis, and flew to New York that afternoon.

While HubSpot chose steak for its Manhattan dinner, HubSpot went Italian, hitting Remi in midtown.

HubSpot, which builds software that helps companies grow by using blogs, analytics, and other tools, got a special surprise when Morgan Stanley, which worked on its initial public offering, brought Shah, Halligan, and some others to Times Square Wednesday evening for a one-of-a-kind photo shoot at the LED board in Times Square.

“They took the ticker symbols off and put HubSpot on there with a $125 million IPO,” Shah said. Morgan Stanley had a photographer across the street capture the moment.

“They told us they’ve only done it for Facebook, Twitter, and now us,” J.D. Sherman, HubSpot’s chief operating officer, said. “It was an exciting night. We had a bunch of folks come down from Boston to celebrate with us. We were just all so excited, it’s hard to sleep after that.”

The next morning, the taxis arrived at their hotel and it was off to the stock exchange for breakfast, the history lesson, the token gifts, and finally, the bell ringing.

Just as Wayfair’s Conine had an emotional moment on the way to the exchange, so did HubSpot’s Shah and his wife Kirsten. When they saw HubSpot’s sprocket logo adorning the stock exchange, it was a moment to pause. Not only was Shah’s company hitting the public market, but it was being represented by the logo that Kirsten herself had designed in the company’s early days.

“It’s hard not to get choked up, with the banner up out front,” Sherman said on the day of HubSpot’s IPO. After pausing to collect his emotions, he said, “It’s pretty awesome…It’s exciting, it’s an exciting day.”

HubSpot, following the lead of its jeans-wearing co-founder, whipped out bright orange sunglasses for its moment, and the team exploded with joy when they rang the bell, prompting one trader to comment that it was the best bell ringing he had seen.

Next, the executives hit the floor, where traders went back and forth on the price of the company’s stock as it is first offered to the public. In a pretty tense half hour of waiting, someone finally shouted, “Here we go,” and the initial price was displayed for all to see. The co-founders rang another ceremonial bell, and HubSpot officially became available for trading.

From there, it was hugs and quick interviews with various media outlets, including some face time on CNBC.

Wayfair and HubSpot were both founded in the Boston area, eschewed the lure of Silicon Valley for downtown Boston and Cambridge respectively, and both have built solid, successful companies in industries that were ripe for innovation: For Wayfair, online furniture sales, for HubSpot, a non-traditional approach to marketing software.

Hours after going public, both Wayfair and HubSpot employees headed back to Boston. The next day, for both companies, it was business as usual, with one exception: The extreme peaks and valleys that the stock market took in the following days took on a whole new meaning.

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