Matt Ostanik
The continuing journey of a truly serial entrepreneur
It is curious how quickly we sometimes pivot from life goals. I found this out about Matt’s life as he and I sipped coffee, the planned 30-minute conversation effortlessly expanding to more than two hours. Matt Ostanik’s career path, originally laid out with an architect’s precision, was shelved to solve a problem all architects faced.
Matt trained to be an architect at Iowa State University; a passion complemented with a childhood desire for entrepreneurship. He graduated with a degree in architecture in 2001, something he continues to cherish. The construction and reporting inefficiencies he discovered, however, proved to be a more fulfilling course. The entrepreneur imagined a new, electronic process to extinguish those inefficiencies and launched his SaaS platform, Submittal Exchange, initially as a side project in 2003.
He wrote a business plan for the project that won a $5000 investment award from the John Pappajohn competition. This validation pushed him to build the first version and raise additional funds to improve and license the platform. This is where he learned a key lesson – building product is much easier than selling it. Even when everyone needs it.
Submittal Exchange solved a type of document management problem faced by architects. Matt, in the weeds with these documents imagined a software product that architects, contractors, and facility owners could use to manage submittals and other documents during the construction process. Finding an industry-specific problem that he faced and knew how to solve, he had found the next step in his journey.
Concurrently, a similar battle was being fought in manufacturing, medicine, law, securities, insurance and government. Some of those battles are familiar to Iowans as they saw the birth of companies such as Workiva in Ames and Gain Compliance in Des Moines focusing on the securities and insurance industries, respectively.
He continued to build Submittal Exchange, supported at home in exchange for a promised return to architecture if the venture didn’t succeed OR if he could sell the company for the proverbial infinite amount – one million dollars. Building while maintaining a full-time job through 2007, success was achieved slowly but progressively - much like a building he was trained to design.
The company success was visible via 35 employees and nearly 40,000 users. I distinctly remember the hub of activity when first visited Submittal Exchange in 2011. An acquisition the same year affirmed Matt’s success metric and paved the way for future businesses and prosperity for owners, investors, and employees.
Matt and his early colleagues were the classic startup team - working all functions of the business from their Adel office. They performed all functions of the business– a pattern repeated in upcoming stories – from hiring and firing, HR, benefits administration, product design and development, sales, support, janitorial, office management and much more. Matt, with his friendly and calm persona, lights up when he speaks of the excitement of those early days, the long hours, the tensions and euphoria juxtaposed with the growing business.
Submittal Exchange was acquired by a strategic buyer, Textura, for cash and stock. Matt was qualified and uniquely positioned to not only run the company but also use his skill and passion to grow through additional acquisitions. Matt was also tapped to be the CEO and ‘fix-it’ guy for another Textura acquisition. He served on the executive team when Textura achieved an IPO in 2013, and revenue and profits grew with Matt’s responsibility, leading ultimately to Oracle Corporation’s acquisition of Textura in 2016.
The entrepreneurial bug resurfaced as Matt began thinking about his talent, experience, and unsolved problems. Matt v3.0 was about to be born – a new journey with new lessons, ones that would include humility. Matt launched Funnelwise in 2013.
The team did so much by long-standing design principles. They talked with potential customers to further refine the problems they’d set out to solve. They studied what the competition was doing well or ignoring. Salesforce, the CRM market leader, provided a tabular, grid-like view of sales leads and opportunities that would excite an accountant more than a sales/marketing leader.
Funnelwise ingested Salesforce data and visually represented it as a funnel where opportunities could visually be seen moving from marketing to sales. Sales leaders could visualize the achievement of their organizational goals, their opportunities, individual performance, and more. The beautiful solution (I saw it first-hand at Funnelwise in mid-2010s) faced a problem many other data projects face - visualized data don’t always provide actionable wisdom - customers didn’t always know what to do with the visually appealing funnels.
Despite increasing turnover on his own team, Matt worked through the challenges reported by customers or observed through their own systems. They added playbooks, a concept marketing consultants call “next best action”. These playbooks provided customers with actionable steps, which failed customer adoption. Customers reported that their data and people weren’t ready yet for these playbooks. They pivoted to solve the data problem through another innovation, SalesEdge but the company was fast approaching the valley of death.
Success in an entrepreneurial venture upon exiting another sometimes eludes successful entrepreneurs. The hunger and desperate need to succeed during of the first company are sometimes shadowed by a desire to repeat the prior formulae. Matt brought his knowledge of this team’s prior sales challenges and lessons into designing Funnelwise. Personal and professional investors’ funds helped build a team and product and formalize the company. The product came to a tough and unrelenting market.
The market also proved to be less ready for the product that Matt envisioned, and despite selling total subscriptions exceeding $1MM, the investment mismatched the growth potential. The Sisyphean task of selling a much-needed product to commercially unviable numbers frustrated the stubborn entrepreneur. Matt acknowledges that in hindsight he should’ve done greater early research, listened more to initial customer feedback, and stopped the investment sooner.
Although Funnelwise and SalesEdge had customers, revenue, and market potential, it entered what the venture world calls the valley of death. In this phase, a company needs sufficient revenue and capital to accelerate growth. Many find this growth through customer revenue from their initial product while others have to rely on investor capital to reach escape velocity. These products, possibly early for their time, couldn’t. Matt outlined this journey remarkably clearly in a LinkedIn post that has become legendary amongst Des Moines startup leaders and remains visible on the company’s LinkedIn page.
Meanwhile, a new idea bubbled.
Though some would judge success by revenue and profits alone, Matt recognized that another measure of success was having the privilege of doing what mattered. His successes through Submittal Exchange, an innate desire to keep building, recognition of the greater purpose in entrepreneurship have all let him to Grateful Giving, his latest startup. Matt lights up when speaking of Impact Investing, a philosophy of coupling the act of philanthropy with greater intention and involvement.
Grateful Giving was born as a way for businesses to exponentially increase the impact of their philanthropy. This amplification, made possible by engaging their customers and employees, creates the network effect possible when individuals connect deeply to a cause. In recent years, large companies with charitable foundations have begun allowing employees to direct company matches to the causes most meaningful to them and not just the company or its foundation. Grateful Giving makes it possible for companies of all sizes, with or without such foundations, to participate in this phenomenon. Employees who share their preferred charities can find and further support companies who support those charities as well. Grateful Giving thus brings the abundance mindset, powered by gratitude, to more people, more companies, and more non-profits serving our world today.
Matt continues to invest in the community of people who contributed to his success and is already planting trees whose shade will arrive long after we are gone from this community. He is a classic example of a technology entrepreneur who built a successful business, reinvested proceeds of its success in the diaspora and community and hasn’t replaced his entrepreneurial hunger with a life of simply chasing sunsets on a golf course. I am grateful for his continued investment in the central Iowa startup community and the time he spent with me telling his story of the continuing journey as a serial entrepreneur.
Source:
Conversation with Matt Ostanik at Lightbrite Coffee, Grimes, IA - Jan 24, 2025
Matt’s conversation with Build Des Moines Magazine, May 2017
LinkedIn - FunnelWise Journey Comes to an End
Grateful Giving Blogs
Funnelwise comes out of the woodworks at the Des Moines Register
I am a proud member of the Iowa Startup Collective, a group of writers exploring entrepreneurship across Iowa. Please check out my peers at this column roundup